US11099479B2 - Resist composition, method of forming resist pattern, polymeric compound, and copolymer - Google Patents
Resist composition, method of forming resist pattern, polymeric compound, and copolymer Download PDFInfo
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- US11099479B2 US11099479B2 US16/334,302 US201716334302A US11099479B2 US 11099479 B2 US11099479 B2 US 11099479B2 US 201716334302 A US201716334302 A US 201716334302A US 11099479 B2 US11099479 B2 US 11099479B2
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- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2051—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source
- G03F7/2059—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source using a scanning corpuscular radiation beam, e.g. an electron beam
Definitions
- the present invention relates to a resist composition, a method of forming a resist pattern, a polymeric compound, and a copolymer.
- Resist materials for use with these types of exposure light sources require lithography properties such as a high resolution capable of reproducing patterns of minute dimensions, and a high level of sensitivity to these types of exposure light sources.
- the developing solution is an alkali developing solution (alkali developing process)
- a chemically amplified positive resist which contains, as a base component (base resin), a resin which exhibits increased solubility in an alkali developing solution under action of acid, and an acid generator is typically used.
- base resin base component
- acid generator an acid generator
- a resist film formed using such a resist composition is selectively exposed at the time of forming a resist pattern, in exposed areas, acid is generated from the acid generator component, and the polarity of the base resin increases by the action of the generated acid, thereby making the exposed areas of the resist film soluble in the alkali developing solution.
- the exposed portions of the resist film are dissolved and removed, whereas the unexposed portions of the resist film remain as patterns, thereby forming a positive resist pattern.
- the base resin used for a chemically amplified resist composition contains a plurality of structural units for improving lithography properties and the like.
- onium salt acid generators such as iodonium salts and sulfonium salts; oxime sulfonate acid generators; diazomethane acid generators; nitrobenzylsulfonate acid generators; iminosulfonate acid generators; and disulfone acid generators are known.
- onium salt acid generators those which have an onium ion such as triphenylsulfonium in the cation moiety are mainly used.
- an alkylsulfonate ion or a fluorinated alkylsulfonate ion in which part or all of the hydrogen atoms within the aforementioned alkylsulfonate ion has been substituted with fluorine atoms is typically used.
- a chemically amplified resist composition which uses, as a base component, a polymeric compound containing a structural unit having an acid decomposable group with a specific structure (an acid decomposable group containing a tertiary carbon atom having bonded thereto an aliphatic hydrocarbon group containing an ether bond) (see, for example, Patent Literature 3).
- Patent Literature 1 Japanese Unexamined Patent Application, First Publication No. 2009-114381
- Patent Document 2 Japanese Unexamined Patent Application, First Publication No. 2012-220800
- the present invention takes the above circumstances into consideration, with an object of providing a novel resin component useful as a base component of a resist composition, a resist composition containing the resin component, and a method of forming a resist pattern using the resist composition.
- a second aspect of the present invention is a method of forming a resist pattern, including: using a resist composition according to the first aspect to form a resist film, exposing the resist film, and developing the exposed resist film to form a resist pattern.
- R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
- Va 0 represents a divalent hydrocarbon group which may have an ether bond;
- n a0 represents an integer of 0 to 2;
- Ra 00 represents an acid dissociable group represented by general formula (a0-r1-1);
- Ra 01 represents a hydrocarbon group which may have a substituent;
- Ra 02 represents a hydrocarbon group which may have a substituent; Ra 01 and Ra 02 may be mutually bonded to form a ring;
- Ya 0 represents a quaternary carbon atom;
- Ra 031 , Ra 032 and Ra 033 each independently represents a hydrocarbon group which may have a substituent; provided that at least one of Ra 031 , Ra 32 and Ra 033 is a hydrocarbon group having a polar group;
- * represents a valence bond.
- R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
- Va 0 represents a divalent hydrocarbon group which may have an ether bond;
- n a0 represents an integer of 0 to 2;
- Ra 00 represents an acid dissociable group represented by general formula (a0-r1-1);
- Ra 01 represents a hydrocarbon group which may have a substituent;
- Ra 02 represents a hydrocarbon group which may have a substituent; Ra 01 and Ra 02 may be mutually bonded to form a ring;
- Ya 0 represents a quaternary carbon atom;
- Ra 031 , Ra 032 and Ra 033 each independently represents a hydrocarbon group which may have a substituent; provided that at least one of Ra 031 , Ra 032 and Ra 033 is a hydrocarbon group having a polar group;
- * represents a valence bond.
- a sixth aspect of the present invention is a copolymer including a structural unit represented by the aforementioned general formula (a0-1) and a structural unit represented by the aforementioned general formula (a10-1).
- a novel resin component useful as a base component of a resist composition a resist composition containing the resin component, and a method of forming a resist pattern using the resist composition.
- sensitivity may be improved in the formation of a resist pattern, and it becomes possible to form a resist pattern exhibiting good lithography properties.
- aliphatic is a relative concept used in relation to the term “aromatic”, and defines a group or compound that has no aromaticity.
- alkyl group includes linear, branched or cyclic, monovalent saturated hydrocarbon, unless otherwise specified. The same applies for the alkyl group within an alkoxy group.
- alkylene group includes linear, branched or cyclic, divalent saturated hydrocarbon, unless otherwise specified.
- a “halogenated alkyl group” is a group in which part or all of the hydrogen atoms of an alkyl group is substituted with a halogen atom.
- the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- the acrylate ester may have the hydrogen atom bonded to the carbon atom on the ⁇ -position substituted with a substituent.
- the substituent (R ⁇ 0 ) that substitutes the hydrogen atom bonded to the carbon atom on the ⁇ -position is an atom other than hydrogen or a group, and examples thereof include an alkyl group of 1 to 5 carbon atoms and a halogenated alkyl group of 1 to 5 carbon atoms.
- a carbon atom on the ⁇ -position of an acrylate ester refers to the carbon atom bonded to the carbonyl group, unless specified otherwise.
- an acrylate ester having the hydrogen atom bonded to the carbon atom on the ⁇ -position substituted with a substituent is sometimes referred to as “ ⁇ -substituted acrylate ester”.
- acrylate esters and ⁇ -substituted acrylate esters are collectively referred to as “( ⁇ -substituted) acrylate ester”.
- an acrylate ester having the hydrogen atom bonded to the carbon atom on the ⁇ -position substituted with a substituent is sometimes referred to as “ ⁇ -substituted acrylate ester”.
- acrylic acid and ⁇ -substituted acrylic acids are collectively referred to as “( ⁇ -substituted) acrylic acid”.
- the acrylamide may have the hydrogen atom bonded to the carbon atom on the ⁇ -position substituted with a substituent, and may have either or both terminal hydrogen atoms on the amino group of acrylamide substituted with a substituent.
- a carbon atom on the ⁇ -position of an acrylamide refers to the carbon atom bonded to the carbonyl group, unless specified otherwise.
- alkyl group as a substituent on the ⁇ -position, a linear or branched alkyl group is preferable, and specific examples include alkyl groups of 1 to 5 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group and a neopentyl group.
- hydroxyalkyl group as the substituent on the ⁇ -position include groups in which part or all of the hydrogen atoms of the aforementioned “alkyl group as the substituent on the ⁇ -position” are substituted with a hydroxy group.
- the number of hydroxy groups within the hydroxyalkyl group is preferably 1 to 5, and most preferably 1.
- the resist composition may be applied to an alkali developing process using an alkali developing solution in the developing treatment, or a solvent developing process using a developing solution containing an organic solvent (organic developing solution) in the developing treatment, and preferably a solvent developing process.
- the resist composition of the present embodiment is preferably a resist composition which forms a positive pattern in an alkali developing process (i.e., a positive resist compound for alkali developing process) or a resist composition which forms a negative pattern in a solvent developing process (i.e., a negative type resist composition for solvent developing process).
- a resist composition (3) in which the component (A) is a component which generates acid upon exposure, and further containing an acid generator component (B).
- the component (A) is a “base component which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid”.
- the component (A1) described later is preferably a polymeric compound which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid.
- the polymeric compound a resin having a structural unit which generates acid upon exposure may be used.
- a conventional structural unit may be used.
- the component (A) is a base component which exhibits changed solubility in a developing solution under action of acid.
- any of those which have a molecular weight of 1,000 or more is generally used.
- a “resin” or a “polymer” refers to a polymer having a molecular weight of 1,000 or more.
- the weight average molecular weight in terms of the polystyrene equivalent value determined by gel permeation chromatography (GPC) is used.
- the component (A) contains a resin component (A1) (hereafter, referred to as “component (A1)”) which exhibits changed solubility in a developing solution by the action of acid.
- component (A1) a resin component (hereafter, referred to as “component (A1)”
- the component (A) at least the component (A1) is used, and a polymeric compound and/or a low molecular weight compound may be used in combination with the component (A1).
- the component (A1) is a polymeric compound including a structural unit (a0) represented by general formula (a0-1), and any other structural unit if desired.
- the component (A1) is substantially insoluble in an alkali developing solution prior to exposure, but when acid is generated from the component (B) upon exposure, the action of this acid causes an increase in the polarity of the base component, thereby increasing the solubility of the component (A1) in an alkali developing solution. Therefore, in the formation of a resist pattern, by conducting selective exposure of a resist film formed by applying the resist composition to a substrate, the exposed portions of the resist film change from an insoluble state to a soluble state in an alkali developing solution, whereas the unexposed portions of the resist film remain insoluble in an alkali developing solution, and hence, a positive resist pattern is formed by alkali developing.
- the component (A1) exhibits high solubility in an organic developing solution prior to exposure, and when acid is generated from the component (B) upon exposure for example, the polarity of the component (A1) is increased by the action of the generated acid, thereby decreasing the solubility of the component (A1) in an organic developing solution. Therefore, in the formation of a resist pattern, by conducting selective exposure of a resist film formed by applying the resist composition to a substrate, the exposed portions of the resist film changes from an soluble state to an insoluble state in an organic developing solution, whereas the unexposed portions of the resist film remain soluble in an organic developing solution. As a result, by conducting development using an organic developing solution, thereby forming a negative resist pattern.
- the structural unit (a0) is represented by general formula (a0-1) shown below.
- the divalent hydrocarbon group for Va 0 may be either an aliphatic hydrocarbon group or an aromatic hydrocarbon group.
- the aliphatic hydrocarbon group as the divalent hydrocarbon group for Va 0 may be either saturated or unsaturated. In general, the aliphatic hydrocarbon group is preferably saturated.
- aliphatic hydrocarbon group a linear or branched aliphatic hydrocarbon group, and an aliphatic hydrocarbon group containing a ring in the structure thereof can be given.
- the aromatic hydrocarbon group as the divalent hydrocarbon group for Va 0 is a hydrocarbon group having an aromatic ring.
- the aromatic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 5 to 30 carbon atoms, still more preferably 5 to 20 carbon atoms, still more preferably 6 to 15 carbon atoms, and most preferably 6 to 10 carbon atoms.
- the number of carbon atoms within a substituent(s) is not included in the number of carbon atoms of the aromatic hydrocarbon group.
- aromatic hydrocarbon groups examples include aromatic hydrocarbon rings, such as benzene, biphenyl, fluorene, naphthalene, anthracene and phenanthrene; and aromatic hetero rings in which part of the carbon atoms constituting the aforementioned aromatic hydrocarbon rings has been substituted with a hetero atom.
- aromatic hetero rings examples include an oxygen atom, a sulfur atom and a nitrogen atom.
- n a0 represents an integer of 0 to 2, preferably 0 or 1, and more preferably 0.
- Ra 00 represents an acid dissociable group represented by general formula (a0-r1-1) shown below.
- the acid dissociable group is a functional group having a quaternary carbon atom (Ya 0 ) and a polar group, and protects the oxy group (—O—) side of the carbonyloxy group [—C( ⁇ O)—O—] in the aforementioned formula (a0-1).
- An “acid dissociable group” exhibits acid dissociability such that the bond between the acid dissociable group and the adjacent oxygen atom (O) is cleaved by the action of acid.
- a polar group which exhibits a higher polarity than the acid dissociable group is generated, and the polarity is increased.
- the polarity of the entire component (A1) is increased.
- Ra 01 represents a hydrocarbon group which may have a substituent
- Ra 02 represents a hydrocarbon group which may have a substituent
- Ra 01 and Ra 02 may be mutually bonded to form a ring
- Ya 0 represents a quaternary carbon atom
- Ra 031 , Ra 032 and Ra 033 each independently represents a hydrocarbon group which may have a substituent; provided that at least one of Ra 031 , Ra 032 and Ra 033 is a hydrocarbon group having a polar group
- “*” represents a valence bond (in the present specification, the same applies hereafter).
- the linear alkyl group for Ra 01 and Ra 02 preferably has 1 to 5 carbon atoms, more preferably 1 to 4 carbon atoms, and still more preferably 1 or 2 carbon atoms.
- Specific examples include a methyl group, an ethyl group, an n-propyl group, an n-butyl group and an n-pentyl group.
- a methyl group, an ethyl group or an n-butyl group is preferable, a methyl group or an ethyl group is more preferable, and a methyl group is still more preferable.
- the branched alkyl group for Ra 01 and Ra 02 preferably has 3 to 10 carbon atoms, and more preferably 3 to 5 carbon atoms.
- Specific examples include an isopropyl group, an isobutyl group, a tert-butyl group, an isopentyl group, a neopentyl group a 1,1-diethylpropyl group and a 2,2-dimethylbutyl group.
- an isopropyl group is preferable.
- the aromatic hydrocarbon group for Ra 01 and Ra 02 is a hydrocarbon group having at least one aromatic ring.
- the aromatic ring is not particularly limited, as long as it is a cyclic conjugated compound having (4n+2) ⁇ electrons, and may be either monocyclic or polycyclic.
- the aromatic ring preferably has 5 to 30 carbon atoms, more preferably 5 to 20, still more preferably 6 to 15, and most preferably 6 to 12.
- Examples of the aromatic ring include aromatic hydrocarbon rings, such as benzene, naphthalene, anthracene and phenanthrene; and aromatic hetero rings in which part of the carbon atoms constituting the aforementioned aromatic hydrocarbon rings has been substituted with a hetero atom.
- hetero atom within the aromatic hetero rings include an oxygen atom, a sulfur atom and a nitrogen atom.
- aromatic hetero ring include a pyridine ring and a thiophene ring.
- aromatic hydrocarbon group include a group in which one hydrogen atom has been removed from the aforementioned aromatic hydrocarbon ring or aromatic hetero ring (aryl group or heteroaryl group); a group in which one hydrogen atom has been removed from an aromatic compound having two or more aromatic rings (biphenyl, fluorene or the like); and a group in which one hydrogen atom of the aforementioned aromatic hydrocarbon ring or aromatic hetero ring has been substituted with an alkylene group (an arylalkyl group such as a benzyl group, a phenethyl group, a 1-naphthylmethyl group, a 2-naphthylmethyl group, a 1-naphthylethyl group, or a 2-naphthyle
- examples of the substituent include a hydroxy group, a carboxy group, a halogen atom (such as a fluorine atom, a chlorine atom or a chlorine atom), an alkoxy group (such as a methoxy group, an ethoxy group, a propoxy group or a butoxy group), and an alkyloxycarbonyl group.
- Ra 01 and Ra 02 may be mutually bonded to form a ring.
- Examples of the ring structure formed by Ra 01 and Ra 02 include an alicyclic hydrocarbon group, and a condensed ring of an alicyclic group and an aromatic hydrocarbon group.
- the ring structure formed by Ra 01 and Ra 02 may have a hetero atom.
- the monocyclic aliphatic hydrocarbon group a group in which 1 hydrogen atom has been removed from a monocycloalkane is preferable.
- the monocycloalkane preferably has 3 to 6 carbon atoms, and specific examples thereof include cyclopentane and cyclohexane.
- the polycyclic aliphatic hydrocarbon group a group in which 1 hydrogen atom has been removed from a polycycloalkane is preferable, and the polycyclic group preferably has 7 to 12 carbon atoms.
- the polycycloalkane include adamantane, norbornane, isobornane, tricyclodecane and tetracyclododecene.
- Ra 01 and Ra 02 are mutually bonded to form a ring, and it is more preferable that Ra 01 and Ra 02 are mutually bonded to form an alicyclic hydrocarbon group.
- the hydrocarbon group (which may have a substituent) for Ra 031 , Ra 032 and Ra 033 is the same as defined for the hydrocarbon group (which may have a substituent) for Ra 01 and Ra 02 in the aforementioned formula (a0-r1-1).
- a linear or branched alkyl group which may have a substituent is preferable, and a linear alkyl group is more preferable.
- Ra 04 represents a divalent hydrocarbon group having 2 to 12 carbon atoms.
- Ra 04 examples include a linear alkanediyl group, such as an ethylene group, a propane-1,3-diyl group, butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, a decane-1,10-diyl group, an undecane-1,11-diyl group, and a dodecane-1,12-diyl group; a branched alkanediyl group, such as a propane-1,2-diyl group, a 1-methylbutane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a pentane-1,4-diyl group
- an alkanediyl group is preferable, and a linear alkanediyl group is more preferable.
- Ra 05 examples include —O—, —C( ⁇ O)—, —C( ⁇ O)—, —O—C( ⁇ O)—O—, —C( ⁇ O)—NH—, —NH—, —NH—C( ⁇ NH)— (H may be substituted with a substituent such as an alkyl group or an acyl group), —S—, —S( ⁇ O) 2 —, and —S( ⁇ O) 2 —O—.
- Ra 06 represents a monovalent hydrocarbon group having 1 to 12 carbon atoms.
- Examples of the hydrocarbon group for Ra 06 include a chain hydrocarbon group, a cyclic hydrocarbon group, and a combination of a chain hydrocarbon group and a cyclic hydrocarbon group.
- the cyclic hydrocarbon group may be an alicyclic hydrocarbon group or an aromatic hydrocarbon group.
- the alicyclic hydrocarbon group may be monocyclic or polycyclic.
- monocyclic alicyclic hydrocarbon groups include cycloalkyl groups, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a dimethylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cycloheptyl group, and a cyclodecyl group.
- polycyclic alicyclic hydrocarbon groups include a decahydronaphthyl group, an adamantyl group, a 2-alkyladamantan-2-yl group, a 1-(adamantan-1-yl)alkan-1-yl group, a norbornyl group, a methylnorbornyl group, and an isonorbornyl group.
- aromatic hydrocarbon groups include a phenyl group, a naphthyl group, an anthryl group, a p-methylphenyl group, a p-tert-butylphenyl group, a p-adamantylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a biphenyl group, a phenanthryl group, 2,6-diethylphenyl group, and 2-methyl-6-ethyl phenyl group.
- Ra 06 is preferably a chain hydrocarbon group, more preferably an alkyl group, and still more preferably a linear alkyl group.
- n p0 is an integer of 1 to 6, preferably an integer of 1 to 3, more preferably 1 or 2, and still more preferably 1.
- At least one of Ra 031 , Ra 032 and Ra 033 is a hydrocarbon group having a polar group.
- the number of hydrocarbon groups having a polar group may be appropriately selected depending on the solubility in the developing solution used in the formation of a resist pattern.
- substituents include a halogen atom (such as a fluorine atom, a chlorine atom or a bromine atom), and a halogenated alkyl group having 1 to 5 carbon atoms.
- Ra 00 is preferably an acid dissociable group represented by general formula (a0-r1-10) shown below.
- Yaa represents a carbon atom
- Xaa represents a group which forms a cyclic hydrocarbon group together with Yaa
- Ya 0 represents a quaternary carbon atom
- Ra 0311 and Ra 0321 each independently represents a chain alkyl group which may have a substituent
- Ra 0331 is a functional group represented by the aforementioned general formula (a0-p 1).
- an alicyclic hydrocarbon group is preferable as the cyclic hydrocarbon group which Xaa forms with Yaa.
- the alicyclic hydrocarbon group may be polycyclic or monocyclic, and is preferably monocyclic.
- the cyclic hydrocarbon group which Xaa forms with Yaa may have a substituent.
- substituents include a hydroxy group, a carboxy group, a halogen atom (such as a fluorine atom, a chlorine atom or a chlorine atom), an alkoxy group (such as a methoxy group, an ethoxy group, a propoxy group or a butoxy group), and an alkyloxycarbonyl group.
- the structural unit (a0) at least one member selected from the group consisting of structural units represented by general formulae (a0-1-1) to (a0-1-9) shown below is preferable, and at least one member selected from the group consisting of structural units represented by general formulae (a0-1-1) to (a0-1-6) shown below is more preferable.
- the structural unit (a0) at least one member selected from the group consisting of structural units represented by formulae (a0-1-1) to (a0-1-3) is most preferable.
- Examples of the polar group include a carboxy group, a hydroxy group, an amino group and a sulfo group (—SO 3 H).
- a polar group containing —OH in the structure thereof (hereafter, referred to as “OH-containing polar group”) is preferable, a carboxy group or a hydroxy group is more preferable, and a carboxy group is particularly desirable.
- an acid decomposable group a group in which the aforementioned polar group has been protected with an acid dissociable group (such as a group in which the hydrogen atom of the OH-containing polar group has been protected with an acid dissociable group) can be given.
- the acid dissociable group that constitutes the acid decomposable group is a group which exhibits a lower polarity than the polar group generated by the dissociation of the acid dissociable group.
- a polar group exhibiting a higher polarity than that of the acid dissociable group is generated, thereby increasing the polarity.
- the polarity of the entire component (A1) is increased.
- acid dissociable groups for the base resin of a conventional chemically amplified resist include “acetal-type acid dissociable group”, “tertiary alkyl ester-type acid dissociable group” and “tertiary alkyloxycarbonyl acid dissociable group” described below.
- Examples of the acid dissociable group for protecting the carboxy group or hydroxy group as a polar group include the acid dissociable group represented by general formula (a1-r-1) shown below (hereafter, referred to as “acetal-type acid dissociable group”).
- Ra′ 1 and Ra′ 2 represents a hydrogen atom or an alkyl group
- Ra′ 3 represents a hydrocarbon group, provided that Ra′ 3 may be bonded to Ra′ 1 or Ra′ 2 .
- Ra′ 1 and Ra′ 2 represent a hydrogen atom
- both of Ra′ 1 and Ra′ 2 represent a hydrogen atom
- Ra′ 1 or Ra′ 2 is an alkyl group
- the same alkyl groups as those described above the for the substituent which may be bonded to the carbon atom on the ⁇ -position of the aforementioned ⁇ -substituted acrylate ester can be mentioned, and an alkyl group of 1 to 5 carbon atoms is preferable. Specific examples include linear or branched alkyl groups.
- the linear alkyl group preferably has 1 to 5 carbon atoms, more preferably 1 to 4, and still more preferably 1 or 2.
- Specific examples include a methyl group, an ethyl group, an n-propyl group, an n-butyl group and an n-pentyl group.
- a methyl group, an ethyl group or an n-butyl group is preferable, and a methyl group or an ethyl group is more preferable.
- the monocyclic aliphatic hydrocarbon group a group in which 1 hydrogen atom has been removed from a monocycloalkane is preferable.
- the monocycloalkane preferably has 3 to 6 carbon atoms, and specific examples thereof include cyclopentane and cyclohexane.
- the polycyclic aliphatic hydrocarbon group a group in which 1 hydrogen atom has been removed from a polycycloalkane is preferable, and the polycyclic group preferably has 7 to 12 carbon atoms.
- the polycycloalkane include adamantane, norbornane, isobornane, tricyclodecane and tetracyclododecene.
- the aromatic hydrocarbon group is a hydrocarbon group having at least one aromatic ring.
- the aromatic ring is not particularly limited, as long as it is a cyclic conjugated compound having (4n+2) ⁇ electrons, and may be either monocyclic or polycyclic.
- the aromatic ring preferably has 5 to 30 carbon atoms, more preferably 5 to 20, still more preferably 6 to 15, and most preferably 6 to 12.
- Examples of the aromatic ring include aromatic hydrocarbon rings, such as benzene, naphthalene, anthracene and phenanthrene; and aromatic hetero rings in which part of the carbon atoms constituting the aforementioned aromatic hydrocarbon rings has been substituted with a hetero atom.
- the hetero atom within the aromatic hetero rings include an oxygen atom, a sulfur atom and a nitrogen atom.
- Specific examples of the aromatic hetero ring include a pyridine ring and a thiophene ring.
- the cyclic group is preferably a 4 to 7-membered ring, and more preferably a 4 to 6-membered ring.
- Specific examples of the cyclic group include tetrahydropyranyl group and tetrahydrofuranyl group.
- Examples of the acid dissociable group for protecting the carboxy group as a polar group include the acid dissociable group represented by general formula (a1-r-2) shown below.
- the acid dissociable groups represented by general formula (a1-r-2) for convenience, a group which is constituted of alkyl groups is referred to as “tertiary ester-type acid dissociable group”.
- Ra′ 12 and Ra′ 14 each independently represents an alkyl group or 1 to 10 carbon atoms, and it is more preferable that the alkyl group is the same group as the described above for the linear or branched alkyl group for Ra′ 3 in the formula (a1-r-1), it is still more preferable that the alkyl group is a linear alkyl group of 1 to 5 carbon atoms, and it is particularly preferable that the alkyl group is a methyl group or an ethyl group.
- Ra′ 13 is the same group as described above for the linear or branched alkyl group or monocyclic or polycyclic alicyclic hydrocarbon group for Ra′ 3 in the formula (a1-r-1).
- monocyclic or polycyclic aliphatic hydrocarbon group for Ra′ 3 are more preferable.
- Examples of the acid dissociable group for protecting a hydroxy group as a polar group include the acid dissociable group represented by general formula (a1-r-3) shown below (hereafter, for convenience, referred to as “tertiary alkyloxycarbonyl-type acid dissociable group”).
- Ra′ 7 to Ra′ 9 each independently represents an alkyl group.
- each of Ra′ 7 to Ra′ 9 is preferably an alkyl group having 1 to 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms.
- the total number of carbon atoms within the alkyl group is preferably 3 to 7, more preferably 3 to 5, and most preferably 3 or 4.
- the structural unit (a1) a structural unit derived from an acrylate ester which may have the hydrogen atom bonded to the carbon atom on the ⁇ -position substituted with a substituent is preferable.
- preferable structural units for the structural unit (a1) include structural units represented by general formula (a1-1) or (a1-2) shown below.
- R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
- Va 1 represents a divalent hydrocarbon group which may contain an ether bond;
- n a1 represents an integer of 0 to 2; and
- Ra 1 represents an acid dissociable group represented by the aforementioned formula (a1-r-1) or (a1-r-2).
- Wa 1 represents a hydrocarbon group having a valency of n a2 +1;
- n a2 represents an integer of 1 to 3; and
- Ra z represents an acid dissociable group represented by the aforementioned formula (a1-r-1) or (a1-r-3).
- R a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a fluorinated alkyl group of 1 to 5 carbon atoms is preferable, and a hydrogen atom or a methyl group is particularly desirable in terms of industrial availability.
- the divalent hydrocarbon group for Va 1 optionally having an ether bond is the same as defined for the divalent hydrocarbon group for Va 0 optionally having an ether bond in general formula (a0-1).
- n a2 +1 is preferably divalent, trivalent or tetravalent, and divalent or trivalent is more preferable.
- R ⁇ represents a hydrogen atom, a methyl group or a trifluoromethyl group.
- 1 type of structural unit may be used, or 2 or more types may be used.
- the amount of the structural unit (a1) based on the combined total of all structural units constituting the component (A1) (100 mol %) is preferably 1 to 50 mol %, more preferably 5 to 45 mol %, and still more preferably 5 to 30 mol %.
- the component (A1) may include, in addition to the structural unit (a0), a structural unit (a2) containing a lactone-containing cyclic group, an —SO 2 — containing cyclic group or a carbonate-containing cyclic group.
- the lactone-containing cyclic group, the —SO 2 — containing cyclic group or the carbonate-containing cyclic group within the structural unit (a2) is effective in improving the adhesion between the resist film and the substrate. Further, by virtue of including the structural unit (a2), in an alkali developing process, during developing, the solubility of the resist film in an alkali developing is enhanced.
- lactone-containing cyclic group refers to a cyclic group including a ring containing a —O—C( ⁇ O)— structure (lactone ring).
- lactone ring refers to a single ring containing a —O—C(O)— structure, and this ring is counted as the first ring.
- a lactone-containing cyclic group in which the only ring structure is the lactone ring is referred to as a monocyclic group, and groups containing other ring structures are described as polycyclic groups regardless of the structure of the other rings.
- the lactone-containing cyclic group may be either a monocyclic group or a polycyclic group.
- the lactone-containing cyclic group for the structural unit (a2) is not particularly limited, and an arbitrary structural unit may be used. Specific examples include groups represented by general formulae (a2-r-1) to (a2-r-7) shown below.
- each Ra′ 21 independently represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a hydroxy group, —COOR′′, —OC( ⁇ O)R′′, a hydroxyalkyl group or a cyano group;
- R′′ represents a hydrogen atom, an alkyl group, a lactone-containing cyclic group, a carbonate-containing cyclic group or an —SO 2 — containing cyclic group;
- A′′ represents an oxygen atom, a sulfur atom, or an alkylene group of 1 to 5 carbon atoms which may contain an oxygen atom or a sulfur atom;
- n′ represents an integer of 0 to 2; and
- m′ represents 0 or 1.
- halogen atom for Ra′ 21 a fluorine atom, chlorine atom, bromine atom and iodine atom can be given. Among these, a fluorine atom is preferable.
- halogenated alkyl group for Ra′ 21 examples include groups in which part or all of the hydrogen atoms within the aforementioned alkyl group for Ra′ 21 has been substituted with the aforementioned halogen atoms.
- a fluorinated alkyl group is preferable, and a perfluoroalkyl group is particularly desirable.
- R′′ is a cyclic alkyl group (cycloalkyl group), it preferably has 3 to 15 carbon atoms, more preferably 4 to 12 carbon atoms, and most preferably 5 to 10 carbon atoms.
- Specific examples include groups in which one or more hydrogen atoms have been removed from a monocycloalkane or a polycycloalkane such as a bicycloalkane, tricycloalkane or tetracycloalkane which may or may not be substituted with a fluorine atom or a fluorinated alkyl group.
- Specific examples include groups in which one or more hydrogen atoms have been removed from a monocycloalkane such as cyclopentane or cyclohexane; and groups in which one or more hydrogen atoms have been removed from a polycycloalkane such as adamantane, norbornane, isobornane, tricyclodecane or tetracyclododecene.
- the —SO 2 — containing cyclic group for R′′ is the same as defined for the —SO 2 -containing cyclic group described later.
- Specific examples of the —SO 2 — containing cyclic group include groups represented by general formulae (a5-r-1) to (a5-r-4).
- the hydroxyalkyl group for Ra′ 21 preferably has 1 to 6 carbon atoms, and specific examples thereof include the alkyl groups for Ra′ 21 in which at least one hydrogen atom has been substituted with a hydroxy group.
- alkylene group of 1 to 5 carbon atoms represented by A′′ a linear or branched alkylene group is preferable, and examples thereof include a methylene group, an ethylene group, an n-propylene group and an isopropylene group.
- alkylene groups that contain an oxygen atom or a sulfur atom include the aforementioned alkylene groups in which —O— or —S— is bonded to the terminal of the alkylene group or present between the carbon atoms of the alkylene group.
- —SO 2 — containing cyclic group examples include groups represented by general formulas (a5-r-1) to (a5-r-4) shown below.
- each Ra′ 51 independently represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, —COOR′′, —OC( ⁇ O)R′′, a hydroxyalkyl group or a cyano group;
- R′′ represents a hydrogen atom, an alkyl group, a lactone-containing cyclic group, a carbonate-containing cyclic group or an —SO 2 — containing cyclic group;
- A′′ represents an oxygen atom, a sulfur atom, or an alkylene group of 1 to 5 carbon atoms with or without an oxygen atom or a sulfur atom;
- n′ represents an integer of 0 to 2.
- A′′ is the same as defined for A′′ in general formulae (a2-r-2), (a2-r-3) and (a2-r-5).
- carbonate-containing cyclic group refers to a cyclic group including a ring containing a —O—C( ⁇ O)—O—structure (carbonate ring).
- carbonate ring refers to a single ring containing a —O—C( ⁇ O)—O—structure, and this ring is counted as the first ring.
- a carbonate-containing cyclic group in which the only ring structure is the carbonate ring is referred to as a monocyclic group, and groups containing other ring structures are described as polycyclic groups regardless of the structure of the other rings.
- the carbonate-containing cyclic group may be either a monocyclic group or a polycyclic group.
- each Ra′ x31 independently represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, —COOR′′, —OC( ⁇ O)R′′, a hydroxyalkyl group or a cyano group;
- R′′ represents a hydrogen atom, an alkyl group, a lactone-containing cyclic group, a carbonate-containing cyclic group or an —SO 2 — containing cyclic group;
- A′′ represents an oxygen atom, a sulfur atom, or an alkylene group of 1 to 5 carbon atoms with or without an oxygen atom or a sulfur atom
- p′ represents an integer of 0 to 3; and q′ is 0 or 1.
- Examples of the alkyl group, alkoxy group, halogen atom, halogenated alkyl group, —COOR′′, —OC( ⁇ O)R′′ and hydroxyalkyl group for Ra′ 31 include the same groups as those described above in the explanation of Ra′ 21 in the general formulas (a2-r-1) to (a2-r-7).
- the structural unit (a2) is preferably a structural unit represented by general formula (a2-1) shown below.
- R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms
- Ya 21 represents a single bond or a divalent linking group
- La 21 represents —O—, —COO—, —CON(R′)—, —OCO—, —CONHCO— or —CONHCS—
- R′ represents a hydrogen atom or a methyl group
- R is the same as defined above.
- R a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a fluorinated alkyl group of 1 to 5 carbon atoms is preferable, and a hydrogen atom or a methyl group is particularly desirable in terms of industrial availability.
- the divalent linking group for Ya 21 is not particularly limited, and preferable examples thereof include a divalent hydrocarbon group which may have a substituent and a divalent linking group containing a hetero atom.
- the divalent hydrocarbon group for Ya 21 is the same as defined for the divalent hydrocarbon group represented by Va 0 in the aforementioned formula (a0-1).
- Examples of the substituent for the divalent hydrocarbon group represented by Ya 21 include an alkyl group of 1 to 5 carbon atoms, an alkoxy group, a halogen atom, a halogenated alkyl group, a hydroxy group, a carbonyl group.
- Ya 21 represents a divalent linking group containing a hetero atom
- the linking group include —O—, —C( ⁇ O)—O—, —C( ⁇ O)—, —O—C( ⁇ O)—O—, —C( ⁇ O)—NH—, —NH—, —NH—C( ⁇ NH)— (may be substituted with a substituent such as an alkyl group, an acyl group or the like), —S—, —S( ⁇ O) 2 —, —S( ⁇ O) 2 —O—, and a group represented by general formula: —Y 21 —O—Y 22 —, —Y 21 —O—, —Y 21 —C( ⁇ O)—O—, —C( ⁇ O)—O—Y 21 —, —[Y 21 —C(O)—O] m′′ —Y 22 —, —Y 21 —O—C(O)—Y 22 — or —Y
- a linear aliphatic hydrocarbon group is preferable, more preferably a linear alkylene group, still more preferably a linear alkylene group of 1 to 5 carbon atoms, and a methylene group or an ethylene group is particularly desirable.
- m′′ represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and most preferably 1.
- the group represented by the formula —[Y 21 —C(O)—O] m ′′-Y 22 — is a group represented by the formula —Y 21 —C( ⁇ O)—O—Y 22 —.
- a group represented by the formula —(CH 2 ) a′ —C( ⁇ O)—O—(CH 2 ) b′ — is preferable.
- Ya 21 preferably represents an ester bond [—C( ⁇ O)—O—], an ether bond (—O—), a linear or branched alkylene group, a combination of these, or a single bond.
- La 21 represents —O—, —COO—, —CON(R′)—, —OCO—, —CONHCO— or —CONHCS—.
- Ra 21 represents a lactone-containing cyclic group, an —SO 2 — containing cyclic group or a carbonate-containing cyclic group.
- lactone-containing cyclic group, the —SO 2 -containing cyclic group and the carbonate-containing cyclic group for Ra 21 include groups represented by general formulae (a2-r-1) to (a2-r-7), groups represented by general formulae (a5-r-1) to (a5-r-4) and groups represented by general formulae (ax3-r-1) to (ax3-r-3).
- Ra 21 a lactone-containing cyclic group or an —SO 2 — containing cyclic group is preferable, and a group represented by the aforementioned general formula (a2-r-1), (a2-r-2), (a2-r-6) or (a5-r-1) is more preferable.
- a group represented by any of chemical formulae (r-lc-1-1) to (r-lc-1-7), (r-lc-2-1) to (r-lc-2-18), (r-lc-6-1), (r-sl-1-1) and (r-sl-1-18) is still more preferable.
- structural unit (a2) contained in the component (A1) 1 kind of structural unit may be used, or 2 or more kinds may be used.
- the amount of the structural unit (a2) based on the combined total (100 mol %) of all structural units constituting the component (A1) is preferably 1 to 70 mol %, more preferably 3 to 60 mol %, and still more preferably 5 to 50 mol %.
- the component (A1) may include, in addition to the structural unit (a0), a structural unit (a3) containing a polar group-containing aliphatic hydrocarbon group (provided that the structural units that fall under the definition of structural units (a0), (a1) and (a2) are excluded).
- the hydrophilicity of the component (A1) is enhanced, thereby contributing to improvement in resolution.
- aliphatic hydrocarbon group examples include linear or branched hydrocarbon groups (preferably alkylene groups) of 1 to 10 carbon atoms, and cyclic aliphatic hydrocarbon groups (cyclic groups). These cyclic groups can be selected appropriately from the multitude of groups that have been proposed for the resins of resist compositions designed for use with ArF excimer lasers.
- the cyclic group is preferably a polycyclic group, more preferably a polycyclic group of 7 to 30 carbon atoms.
- structural units derived from an acrylate ester that include an aliphatic polycyclic group that contains a hydroxyl group, cyano group, carboxyl group or a hydroxyalkyl group in which part of the hydrogen atoms of the alkyl group have been substituted with fluorine atoms are particularly desirable.
- the polycyclic group include groups in which two or more hydrogen atoms have been removed from a bicycloalkane, tricycloalkane, tetracycloalkane or the like.
- groups in which two or more hydrogen atoms have been removed from a polycycloalkane such as adamantane, norbornane, isobornane, tricyclodecane or tetracyclododecene.
- adamantane norbornane
- isobornane tricyclodecane or tetracyclododecene.
- groups in which two or more hydrogen atoms have been removed from adamantane, norbornane or tetracyclododecene are preferred industrially.
- the structural unit (a3) there is no particular limitation as long as it is a structural unit containing a polar group-containing aliphatic hydrocarbon group, and an arbitrary structural unit may be used.
- the structural unit (a3) is preferably a structural unit derived from an acrylate ester which may have the hydrogen atom bonded to the carbon atom on the ⁇ -position substituted with a substituent and contains a polar group-containing aliphatic hydrocarbon group.
- R is the same as defined above; j is an integer of 1 to 3; k is an integer of 1 to 3; t′ is an integer of 1 to 3; 1 is an integer of 1 to 5; and s is an integer of 1 to 3.
- j is preferably 1 or 2, and more preferably 1.
- j is 2, it is preferable that the hydroxyl groups be bonded to the 3rd and 5th positions of the adamantyl group.
- j is 1, it is preferable that the hydroxyl group be bonded to the 3rd position of the adamantyl group.
- j is preferably 1, and it is particularly desirable that the hydroxyl group be bonded to the 3rd position of the adamantyl group.
- t′ is preferably 1.
- l is preferably 1.
- s is preferably 1.
- a 2-norbornyl group or 3-norbornyl group be bonded to the terminal of the carboxy group of the acrylic acid.
- the fluorinated alkyl alcohol is preferably bonded to the 5th or 6th position of the norbornyl group.
- the amount of the structural unit (a3) based on the combined total (100 mol %) of all structural units constituting the component (A1) is preferably 1 to 50 mol %, more preferably 1 to 40 mol %, still more preferably 3 to 30 mol %, and most preferably 10 to 20 mol %.
- the amount of the structural unit (a3) is at least as large as the lower limit of the above-mentioned preferable range, the resolution is improved in the formation of a resist pattern.
- the amount of the structural unit (a3) is no more than the upper limit of the above-mentioned preferable range, a good balance can be reliably achieved with the other structural units.
- the component (A1) may be further include, in addition to the structural unit (a0), a structural unit (a4) containing an acid non-dissociable, aliphatic cyclic group.
- the component (A1) includes the structural unit (a4)
- dry etching resistance of the resist pattern to be formed is improved.
- the hydrophobicity of the component (A) is further improved. Increase in the hydrophobicity contributes to improvement in terms of resolution, shape of the resist pattern and the like, particularly in a solvent developing process.
- an “acid non-dissociable, aliphatic cyclic group” in the structural unit (a4) refers to a cyclic group which is not dissociated by the action of the acid (e.g., acid generated from a structural unit which generates acid upon exposure or acid generated from the component (B)) upon exposure, and remains in the structural unit.
- At least one polycyclic group selected from amongst a tricyclodecyl group, adamantyl group, tetracyclododecyl group, isobornyl group, and norbornyl group is particularly desirable.
- These polycyclic groups may be substituted with a linear or branched alkyl group of 1 to 5 carbon atoms.
- structural unit (a4) include structural units represented by general formulae (a4-1) to (a4-7) shown below.
- 1 type of structural unit may be used, or 2 or more types may be used.
- the amount of the structural unit (a4) is at least as large as the lower limit of the above-mentioned preferable range, the effect of using the structural unit (a4) can be satisfactorily achieved.
- the amount of the structural unit (a4) is no more than the upper limit of the above-mentioned preferable range, a good balance can be achieved with the other structural units.
- Structural unit derived from styrene or a derivative thereof structural unit (st)
- styrene is a concept including styrene and compounds in which the hydrogen atom at the ⁇ -position of styrene is substituted with a substituent such as an alkyl group or a halogenated alkyl group.
- a substituent such as an alkyl group or a halogenated alkyl group.
- alkyl group as the substituent include an alkyl group having 1 to 5 carbon atoms.
- halogenated alkyl group as the substituent include a halogenated alkyl group having 1 to 5 carbon atoms.
- styrene derivative examples include styrene which has a substituent other than a hydroxy group bonded to the benzene ring and may have the hydrogen atom on the ⁇ -position substituted with a substituent.
- the ⁇ -position (carbon atom on the ⁇ -position) refers to the carbon atom having the benzene ring bonded thereto, unless specified otherwise.
- a “structural unit derived from styrene” or “structural unit derived from a styrene derivative” refers to a structural unit that is formed by the cleavage of the ethylenic double bond of styrene or a styrene derivative.
- the amount of the structural unit (st) based on the combined total of all structural units constituting the component (A1) (100 mol %) is preferably 1 to 30 mol %, and more preferably 3 to 20 mol %.
- Examples of the component (A1) include a polymeric compound having a structural unit (a0) and a structural unit (a2); and a polymeric compound having structural unit (a0), a structural unit (a2) and a structural unit (a3).
- a copolymer having a repeating structure of the structural units (a0), (a2) and (a3) is preferable.
- the weight average molecular weight (Mw) (the polystyrene equivalent value determined by gel permeation chromatography (GPC)) of the component (A1) is not particularly limited, but is preferably 1,000 to 500,000, more preferably 2,000 to 100,000, and still more preferably 3,000 to 50,000.
- the molecular weight dispersity (Mw/Mn) of the component (A1) is not particularly limited, but is preferably 1.0 to 4.0, more preferably 1.0 to 3.0, and most preferably 1.5 to 2.5.
- Mn is the number average molecular weight.
- one kind of resin may be used, or two or more kinds of resins may be used.
- the amount of the component (A1) based on the total weight of the component (A) is preferably 25% by weight or more, more preferably 50% by weight or more, still more preferably 75% by weight or more, and may be even 100% by weight.
- the amount of the component (A1) is at least as large as the lower limit of the above preferable range, sensitivity may be improved, and a resist pattern with improved lithography properties such improved roughness may be reliably formed.
- component (A2) a base component which exhibits changed solubility in a developing solution under action of acid
- component (A2) a base component which exhibits changed solubility in a developing solution under action of acid
- component (A2) there is no particular limitation, and any of the multitude of conventional base resins used within chemically amplified resist compositions may be arbitrarily selected for use.
- one kind of resin may be used, or two or more kinds of resins may be used.
- the component (A) one kind of compound may be used, or two or more kinds of compounds may be used in combination.
- the amount of the component (A) may be appropriately adjusted depending on the thickness of the resist film to be formed, and the like.
- the resist composition of the present embodiment may contain, in addition to the aforementioned component (A), any other components other than the component (A).
- the other components include the component (B), the component (D), the component (E), the component (F) and the component (S) described below.
- the resist composition of the present embodiment may include, in addition to the components (A), an acid-generator component (hereafter, sometimes referred to as “component (B)”).
- component (B) an acid-generator component
- Examples of these acid generators are numerous, and include onium salt acid generators such as iodonium salts and sulfonium salts; oxime sulfonate acid generators; diazomethane acid generators such as bisalkyl or bisaryl sulfonyl diazomethanes and poly(bis-sulfonyl)diazomethanes; nitrobenzylsulfonate acid generators; iminosulfonate acid generators; and disulfone acid generators.
- onium salt acid generators such as iodonium salts and sulfonium salts
- oxime sulfonate acid generators diazomethane acid generators such as bisalkyl or bisaryl sulfonyl diazomethanes and poly(bis-sulfonyl)diazomethanes
- nitrobenzylsulfonate acid generators iminosulfonate acid generators
- R 101 represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent.
- the cyclic group is preferably a cyclic hydrocarbon group, and the cyclic hydrocarbon group may be either an aromatic hydrocarbon group or an aliphatic hydrocarbon group.
- An “aliphatic hydrocarbon group” refers to a hydrocarbon group that has no aromaticity.
- the aliphatic hydrocarbon group may be either saturated or unsaturated, but in general, the aliphatic hydrocarbon group is preferably saturated.
- Examples of the aromatic ring contained in the aromatic hydrocarbon group represented by R 101 include benzene, fluorene, naphthalene, anthracene, phenanthrene and biphenyl; and aromatic hetero rings in which part of the carbon atoms constituting the aforementioned aromatic rings has been substituted with a hetero atom.
- Examples of the hetero atom within the aromatic hetero rings include an oxygen atom, a sulfur atom and a nitrogen atom.
- an alicyclic hydrocarbon group (a group in which one hydrogen atom has been removed from an aliphatic hydrocarbon ring), a group in which the alicyclic hydrocarbon group is bonded to the terminal of the aforementioned chain-like aliphatic hydrocarbon group, and a group in which the alicyclic group is interposed within the aforementioned linear or branched aliphatic hydrocarbon group, can be given.
- the alicyclic hydrocarbon group may be either a polycyclic group or a monocyclic group.
- the monocyclic alicyclic hydrocarbon group a group in which one or more hydrogen atoms have been removed from a monocycloalkane is preferable.
- the monocycloalkane preferably has 3 to 6 carbon atoms, and specific examples thereof include cyclopentane and cyclohexane.
- the polycyclic alicyclic hydrocarbon group a group in which one or more hydrogen atoms have been removed from a polycycloalkane is preferable, and the polycyclic group preferably has 7 to 30 carbon atoms.
- cyclic aliphatic hydrocarbon group for R 101 a group in which one or more hydrogen atoms have been removed from a monocycloalkane or a polycycloalkane is preferable, a group in which one or more hydrogen atoms have been removed from a polycycloalkane is more preferable, an adamantyl group or a norbornyl group is still more preferable, and an adamantyl group is most preferable.
- the linear or branched aliphatic hydrocarbon group which may be bonded to the alicyclic hydrocarbon group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms, and most preferably 1 to 3 carbon atoms.
- a linear alkylene group is preferable. Specific examples thereof include a methylene group [—CH 2 —], an ethylene group [—(CH 2 ) 2 —], a trimethylene group [—(CH 2 ) 3 —], a tetramethylene group [—(CH 2 ) 4 -] and a pentamethylene group [—(CH 2 ) 5 —].
- branched alkylene groups are preferred, and specific examples include various alkylalkylene groups, including alkylmethylene groups such as —CH(CH 3 )—, —CH(CH 2 CH 3 )—, —C(CH 3 ) 2 —, —C(CH 3 )(CH 2 CH 3 )—, —C(CH 3 )(CH 2 CH 2 CH 3 )—, and —C(CH 2 CH 3 ) 2 —; alkylethylene groups such as —CH(CH 3 )CH 2 —, —CH(CH 3 )CH(CH 3 )—, —C(CH 3 ) 2 CH 2 —, —CH(CH 2 CH 3 )CH 2 —, and —C(CH 2 CH 3 ) 2 —CH 2 —; alkyltrimethylene groups such as —CH(CH 3 )CH 2 CH 2 —, and —CH 2 CH(CH 3 )CH 2 —; and
- an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a hydroxyl group, a carbonyl group, a nitro group or the like can be used as the substituent for the cyclic group for R 101 .
- the alkyl group as the substituent is preferably an alkyl group of 1 to 5 carbon atoms, and a methyl group, an ethyl group, a propyl group, an n-butyl group or a tert-butyl group is particularly desirable.
- halogen atom for the substituent examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferable.
- Example of the aforementioned halogenated alkyl group includes a group in which a part or all of the hydrogen atoms within an alkyl group of 1 to 5 carbon atoms (e.g., a methyl group, an ethyl group, a propyl group, an n-butyl group or a tert-butyl group) have been substituted with the aforementioned halogen atoms.
- an alkyl group of 1 to 5 carbon atoms e.g., a methyl group, an ethyl group, a propyl group, an n-butyl group or a tert-butyl group
- the carbonyl group as the substituent is a group that substitutes a methylene group (—CH 2 —) constituting the cyclic hydrocarbon group.
- Chain alkyl group which may have a substituent:
- the linear alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, and still more preferably 1 to 10 carbon atoms.
- Specific examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, an isotridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, an isohexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, a henicosyl group
- the branched alkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, and still more preferably 3 to 10 carbon atoms.
- Specific examples include a 1-methylethyl group, a 1-methylpropyl group, a 2-methylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 1-ethylbutyl group, a 2-ethylbutyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group and a 4-methylpentyl group.
- Chain alkenyl group which may have a substituent:
- the chain-like alkenyl group for R 101 may be linear or branched, and preferably has 2 to 10 carbon atoms, more preferably 2 to 5 carbon atoms, still more preferably 2 to 4 carbon atoms, and most preferably 3 carbon atoms.
- linear alkenyl groups include a vinyl group, a propenyl group (an allyl group) and a butynyl group.
- branched alkenyl groups include a 1-methylvinyl group, a 2-methylvinyl group, a 1-methylpropenyl group and a 2-methylpropenyl group.
- an alkoxy group, a halogen atom, a halogenated alkyl group, a hydroxyl group, a carbonyl group, a nitro group, an amino group, a cyclic group for R 101 or the like can be used.
- Y 101 may contain an atom other than an oxygen atom.
- atoms other than an oxygen atom include a carbon atom, a hydrogen atom, a sulfur atom and a nitrogen atom.
- divalent linking groups containing an oxygen atom examples include non-hydrocarbon, oxygen atom-containing linking groups such as an oxygen atom (an ether bond; —O—), an ester bond (—C( ⁇ O)—O—), an oxycarbonyl group (—O—C( ⁇ O)—), an amido bond (—C( ⁇ O)—NH—), a carbonyl group (—C( ⁇ O)—) and a carbonate bond (—O—C( ⁇ O)—O—); and combinations of the aforementioned non-hydrocarbon, hetero atom-containing linking groups with an alkylene group. Furthermore, the combinations may have a sulfonyl group (—SO 2 —) bonded thereto. Examples of divalent linking groups containing an oxygen atom include linking groups represented by general formulae (y-a1-1) to (y-a1-7) shown below.
- the alkylene group for V′ 101 and V′ 102 may be a linear alkylene group or a branched alkylene group, and a linear alkylene group is preferable.
- alkylene group for V′ 101 and V′ 102 include a methylene group [—CH 2 —]; an alkylmethylene group, such as —CH(CH 3 )—, —CH(CH 2 CH 3 )—, —C(CH 3 ) 2 —, —C(CH 3 )(CH 2 CH 3 )—, —C(CH 3 )(CH 2 CH 2 CH 3 )— and —C(CH 2 CH 3 ) 2 —; an ethylene group [—CH 2 CH 2 —]; an alkylethylene group, such as —CH(CH 3 )CH 2 —, —CH(CH 3 )CH(CH 3 )—, —C(CH 3 ) 2 CH 2 — and —CH(CH 2 CH 3 )CH 2 —; a trimethylene group (n-propylene group) [—CH 2 CH 2 CH 2 —]; an alkyltrimethylene group, such as —CH(CH 3 )CH 2 CH 2
- Y 101 is preferably a divalent linking group containing an ether bond or a divalent linking group containing an ester bond, and groups represented by the aforementioned formulas (y-a1-1) to (y-a1-5) are preferable.
- V 101 represents a single bond, an alkylene group or a fluorinated alkylene group.
- the alkylene group and the fluorinated alkylene group for V 101 preferably has 1 to 4 carbon atoms.
- the fluorinated alkylene group for V 101 include a group in which part or all of the hydrogen atoms within the alkylene group for V 101 have been substituted with fluorine.
- V 101 a single bond or a fluorinated alkylene group of 1 to 4 carbon atoms is preferable.
- a fluorinated alkylsulfonate anion such as a trifluoromethanesulfonate anion or a perfluorobutanesulfonate anion can be mentioned; and in the case where Y 101 represents a divalent linking group containing an oxygen atom, anions represented by formulae (an-1) to (an-3) shown below can be mentioned.
- R′′ 101 , R′′ 102 and R′′ 103 which may have a substituent
- the same groups as the cyclic aliphatic hydrocarbon group for R 101 described above are preferable.
- the same groups as those described above for substituting the cyclic aliphatic hydrocarbon group for R 101 can be mentioned.
- the same groups as the aromatic hydrocarbon group for the cyclic hydrocarbon group represented by R 101 described above are preferable.
- the substituent is the same as defined for the substituent for the aromatic hydrocarbon group represented by R 101 .
- chain-like alkyl group for R′′ 101 which may have a substituent
- chain-like alkenyl group for R′′ 103 which may have a substituent
- the same groups as those described above for R 101 are preferable.
- R 104 and R 105 a chain-like alkyl group which may have a substituent is preferable, and a linear or branched alkyl group or a linear or branched fluorinated alkyl group is more preferable.
- R 106 to R 108 each independently represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent, and is the same as defined for R 101 in formula (b-1).
- m represents an integer of 1 or more
- M′ m+ represents an onium cation having a valency of m, preferably a sulfonium cation or an iodonium cation, and most preferably an organic cation represented by any one of the following formulae (ca-1) to (ca-5).
- R 201 to R 207 , R 211 and R 212 each independently represents an aryl group, an alkyl group or an alkenyl group, provided that two of R 201 to R 203 , R 206 and R 207 , or R 211 and R 212 may be mutually bonded to form a ring with the sulfur atom;
- R 208 and R 209 each independently represents a hydrogen atom or an alkyl group of 1 to 5 carbon atoms;
- R 210 represents an aryl group which may have a substituent, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or an —SO 2 -containing cyclic group which may have a substituent;
- L 201 represents —C( ⁇ O)— or —C( ⁇ O)—O—;
- Y 201 each independently represents an arylene group, an alkylene group or an alkenylene group;
- x represents 1 or 2; and
- W 201
- the alkyl group for R 201 to R 207 , R 211 and R 212 is preferably a chain-like or cyclic alkyl group having 1 to 30 carbon atoms.
- the alkenyl group for R 201 to R 207 , R 211 and R 212 preferably has 2 to 10 carbon atoms.
- R 201 to R 207 and R 210 to R 212 may have include an alkyl group, a halogen atom, a halogenated alkyl group, a carbonyl group, a cyano group, an amino group, an aryl group, and groups represented by formulae (ca-r-1) to (ca-r-7) shown below.
- each R′ 201 independently represents a hydrogen atom, a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent.
- the chain-like alkyl group which may have a substituent and the chain-like alkenyl group which may have a substituent for R′ 201 the same groups as those described above for R 101 can be mentioned.
- the cyclic group which may have a substituent and chain-like alkyl group which may have a substituent the same groups as those described above for the acid dissociable group represented by the aforementioned formula (a1-r-2) can be also mentioned.
- the ring containing the sulfur atom in the skeleton thereof is preferably a 3 to 10-membered ring, and most preferably a 5 to 7-membered ring.
- Specific examples of the ring formed include a thiophene ring, a thiazole ring, a benzothiophene ring, a thianthrene ring, a benzothiophene ring, a dibenzothiophene ring, a 9H-thioxanthene ring, a thioxanthone ring, a phenoxathiin ring, a tetrahydrothiophenium ring, and a tetrahydrothiopyranium ring.
- R 208 and R 209 each independently represents a hydrogen atom or an alkyl group of 1 to 5 carbon atoms, preferably a hydrogen atom or an alkyl group of 1 to 3 carbon atoms, and when R 208 and R 209 each represents an alkyl group, R 208 and R 209 may be mutually bonded to form a ring.
- R 210 represents an aryl group which may have a substituent, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or an —SO 2 — containing cyclic group which may have a substituent.
- the alkenyl group for R 210 preferably has 2 to 10 carbon atoms.
- the —SO 2 — containing cyclic group for R 210 which may have a substituent is the same as defined for the —SO 2 — containing cyclic group represented by any of the aforementioned general formulae (a5-r-1) to (a5-r-4).
- the “—SO 2 — containing polycyclic group” is preferable, and a group represented by general formula (a5-r-1) is more preferable.
- each Y 20′ independently represents an arylene group, an alkylene group or an alkenylene group.
- W 201 represents a linking group having a valency of (x+1), i.e., a divalent or trivalent linking group.
- the divalent linking group for W 201 a divalent hydrocarbon group which may have a substituent is preferable, and as examples thereof, the same hydrocarbon groups (which may have a substituent) as those described above for Ya 21 in the general formula (a2-1) can be mentioned.
- the divalent linking group for W 201 may be linear, branched or cyclic, and cyclic is more preferable.
- an arylene group having two carbonyl groups, each bonded to the terminal thereof is preferable.
- the arylene group include a phenylene group and a naphthylene group, and a phenylene group is particularly desirable.
- the trivalent linking group for W 201 a group in which one hydrogen atom has been removed from the aforementioned divalent linking group for W 201 and a group in which the divalent linking group has been bonded to another divalent linking group can be mentioned.
- the trivalent linking group for W 201 is preferably a group in which 2 carbonyl groups are bonded to an arylene group.
- g1, g2 and g3 represent recurring numbers, wherein g1 is an integer of 1 to 5, g2 is an integer of 0 to 20, and g3 is an integer of 0 to 20.
- preferable cations represented by the formula (ca-2) include a diphenyliodonium cation and a bis(4-tert-butylphenyl)iodonium cation.
- preferable cations represented by formula (ca-4) include cations represented by formulae (ca-4-1) and (ca-4-2) shown below.
- examples of preferable cations represented by formula (ca-5) include cations represented by formulae (ca-5-1) to (ca-5-3) shown below.
- a cation represented by general formula (ca-1) is preferable, and a cation represented by any one of formulae (ca-1-1) to (ca-1-72) is more preferable.
- one type of these acid generators may be used alone, or two or more types may be used in combination.
- the amount of the component (B) relative to 100 parts by weight of the component (A) is preferably within a range from 0.5 to 60 parts by weight, more preferably from 1 to 50 parts by weight, and still more preferably from 1 to 40 parts by weight.
- the amount of the component (B) is within the above-mentioned range, formation of a resist pattern can be satisfactorily performed. Further, by virtue of the above-mentioned range, when each of the components are dissolved in an organic solvent, a homogeneous solution may be more reliably obtained and the storage stability of the resist composition becomes satisfactory.
- the resist composition according to the present embodiment may include an acid diffusion control agent component (hereafter, sometimes referred to as “component (D)”), in addition to the component (A), or in addition to the component (A) and the component (B).
- component (D) functions as an acid diffusion control agent, i.e., a quencher which traps the acid generated in the resist composition upon exposure.
- the component (D) may be a photodecomposable base (D1) (hereafter, referred to as “component (D1)”) which is decomposed upon exposure and then loses the ability of controlling of acid diffusion, or a nitrogen-containing organic compound (D2) (hereafter, referred to as “component (D2)”) which does not fall under the definition of component (D1).
- component (D1) a photodecomposable base
- component (D2) hereafter, referred to as “component (D2)
- the component (D1) is not particularly limited, as long as it is decomposed upon exposure and then loses the ability of controlling of acid diffusion.
- As the component (D1) at least one compound selected from the group consisting of a compound represented by general formula (d1-1) shown below (hereafter, referred to as “component (d1-1)”), a compound represented by general formula (d1-2) shown below (hereafter, referred to as “component (d1-2)”) and a compound represented by general formula (d1-3) shown below (hereafter, referred to as “component (d1-3)”) is preferably used.
- the components (d1-1) to (d1-3) are decomposed and then lose the ability of controlling of acid diffusion (i.e., basicity), and therefore the components (d1-1) to (d1-3) cannot function as a quencher, whereas at unexposed portions, the components (d1-1) to (d1-3) functions as a quencher.
- Rd 1 to Rd 4 represent a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent, provided that, the carbon atom adjacent to the sulfur atom within the Rd 2 in the formula (d1-2) has no fluorine atom bonded thereto;
- Yd 1 represents a single bond or a divalent linking group;
- m represents an integer of 1 or more; and each M m+ independently represents an organic cation having a valency of m.
- Rd 1 represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent, and is the same groups as those defined above for R 101 in the aforementioned formula (b-1).
- the substituent may be bonded via an alkylene group, and a linking group represented by any one of the aforementioned formulae (y-a1-1) to (y-a1-5) is preferable as the substituent.
- the aromatic hydrocarbon group is preferably a phenyl group or a naphthyl group.
- Examples of the aliphatic cyclic group include groups in which one or more hydrogen atoms have been removed from a polycycloalkane such as adamantane, norbornane, isobornane, tricyclodecane or tetracyclododecene.
- the chain-like alkyl group preferably has 1 to 10 carbon atoms, and specific examples thereof include a linear alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl or a decyl group, and a branched alkyl group such as a 1-methylethyl group, a 1-methylpropyl group, a 2-methylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 1-ethylbutyl group, a 2-ethylbutyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group or a 4-methylpentyl group.
- a linear alkyl group such as a
- the chain-like alkyl group is a fluorinated alkyl group having a fluorine atom or a fluorinated alkyl group
- the fluorinated alkyl group preferably has 1 to 11 carbon atoms, more preferably 1 to 8 carbon atoms, and still more preferably 1 to 4 carbon atoms.
- the fluorinated alkyl group may contain an atom other than fluorine. Examples of the atom other than fluorine include an oxygen atom, a sulfur atom and a nitrogen atom.
- a fluorinated alkyl group in which part or all of the hydrogen atoms constituting a linear alkyl group have been substituted with fluorine atom(s) is preferable, and a fluorinated alkyl group in which all of the hydrogen atoms constituting a linear alkyl group have been substituted with fluorine atoms (i.e., a linear perfluoroalkyl group) is particularly desirable.
- one kind of compound may be used, or two or more kinds of compounds may be used in combination.
- Rd 2 represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent, and is the same groups as those defined above for R 101 in the aforementioned formula (b-1).
- M m+ is an organic cation having a valency of m, and is the same as defined for M m+ in the aforementioned formula (d1-1).
- one type of compound may be used, or two or more types of compounds may be used in combination.
- Rd 3 represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent, and is the same groups as those defined above for R 101 in the aforementioned formula (b-1), and a cyclic group containing a fluorine atom, a chain-like alkyl group or a chain-like alkenyl group is preferable.
- a fluorinated alkyl group is preferable, and more preferably the same fluorinated alkyl groups as those described above for Rd 1 .
- Rd 4 represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent, and is the same groups as those defined above for R 101 in the aforementioned formula (b-1).
- an alkyl group which may have substituent an alkoxy group which may have substituent, an alkenyl group which may have substituent or a cyclic group which may have substituent is preferable.
- the alkyl group for Rd 4 is preferably a linear or branched alkyl group of 1 to 5 carbon atoms, and specific examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group, and a neopentyl group.
- Part of the hydrogen atoms within the alkyl group for Rd 4 may be substituted with a hydroxy group, a cyano group or the like.
- the alkoxy group for Rd 4 is preferably an alkoxy group of 1 to 5 carbon atoms, and specific examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group and a tert-butoxy group. Among these, a methoxy group and an ethoxy group are preferable.
- alkenyl group for Rd 4 the same groups as those described above for R 101 in the aforementioned formula (b-1) can be mentioned, and a vinyl group, a propenyl group (an allyl group), a 1-methylpropenyl group and a 2-methylpropenyl group are preferable. These groups may have an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms as a substituent.
- cyclic group for Rd 4 the same groups as those described above for R 101 in the aforementioned formula (b-1) can be mentioned.
- cyclic group an alicyclic group (e.g., a group in which one or more hydrogen atoms have been removed from a cycloalkane such as cyclopentane, cyclohexane, adamantane, norbornane, isobornane, tricyclodecane or tetracyclododecene) or an aromatic group (e.g., a phenyl group or a naphthyl group) is preferable.
- a cycloalkane such as cyclopentane, cyclohexane, adamantane, norbornane, isobornane, tricyclodecane or tetracyclododecene
- aromatic group e.g., a phenyl group or a naphthyl group
- Yd 1 represents a single bond or a divalent linking group.
- the divalent linking group for Yd 1 is not particularly limited, and examples thereof include a divalent hydrocarbon group (aliphatic hydrocarbon group, or aromatic hydrocarbon group) which may have a substituent and a divalent linking group containing a hetero atom.
- the divalent linking groups are the same as defined for the divalent hydrocarbon group which may have a substituent and the divalent linking group containing a hetero atom explained above as the divalent linking group for Ya 21 in the aforementioned formula (a2-1).
- Yd 1 a carbonyl group, an ester bond, an amide bond, an alkylene group or a combination of these is preferable.
- alkylene group a linear or branched alkylene group is more preferable, and a methylene group or an ethylene group is still more preferable.
- M m+ is an organic cation having a valency of m, and is the same as defined for M m+ in the aforementioned formula (d1-1).
- component (D1) one type of the aforementioned components (d1-1) to (d1-3), or at least two types of the aforementioned components (d1-1) to (d1-3) can be used in combination.
- the amount of the component (D1) relative to 100 parts by weight of the component (A) is preferably within a range from 0.5 to 10 parts by weight, more preferably from 0.5 to 8 parts by weight, and still more preferably from 1 to 8 parts by weight.
- the amount of the component (D1) is at least as large as the lower limit of the above-mentioned range, excellent lithography properties and excellent resist pattern shape can be more reliably obtained.
- the amount of the component (D1) is no more than the upper limit of the above-mentioned range, sensitivity can be maintained at a satisfactory level, and through-put becomes excellent.
- the production methods of the components (d1-1) and (d1-2) are not particularly limited, and the components (d1-1) and (d1-2) can be produced by conventional methods.
- the production method of the component (d1-3) is not particularly limited, and the component (d1-3) can be produced in the same manner as disclosed in US2012-0149916.
- the acid diffusion control component may contain a nitrogen-containing organic compound (D2) (hereafter, referred to as component (D2)) which does not fall under the definition of component (D 1).
- D2 nitrogen-containing organic compound
- the component (D2) is not particularly limited, as long as it functions as an acid diffusion control agent, and does not fall under the definition of the component (D1).
- any of the conventionally known compounds may be selected for use. Among these, an aliphatic amine is preferable, and a secondary aliphatic amine or tertiary aliphatic amine is more preferable.
- An aliphatic amine is an amine having one or more aliphatic groups, and the aliphatic groups preferably have 1 to 12 carbon atoms.
- aliphatic amines examples include amines in which at least one hydrogen atom of ammonia (NH 3 ) has been substituted with an alkyl group or hydroxyalkyl group of no more than 12 carbon atoms (i.e., alkylamines or alkylalcoholamines), and cyclic amines.
- NH 3 hydrogen atom of ammonia
- alkylamines and alkylalcoholamines include monoalkylamines such as n-hexylamine, n-heptylamine, n-octylamine, n-nonylamine, and n-decylamine; dialkylamines such as diethylamine, di-n-propylamine, di-n-heptylamine, di-n-octylamine, and dicyclohexylamine; trialkylamines such as trimethylamine, triethylamine, tri-n-propylamine, tri-n-butylamine, tri-n-hexylamine, tri-n-pentylamine, tri-n-heptylamine, tri-n-octylamine, tri-n-nonylamine, tri-n-decylamine, and tri-n-dodecylamine; and alkyl alcohol amines such as diethanolamine, triethanolamine, di
- Examples of the cyclic amine include heterocyclic compounds containing a nitrogen atom as a hetero atom.
- the heterocyclic compound may be a monocyclic compound (aliphatic monocyclic amine), or a polycyclic compound (aliphatic polycyclic amine).
- aliphatic monocyclic amine examples include piperidine, and piperazine.
- the aliphatic polycyclic amine preferably has 6 to 10 carbon atoms, and specific examples thereof include 1,5-diazabicyclo[4.3.0]-5-nonene, 1,8-diazabicyclo[5.4.0]-7-undecene, hexamethylenetetramine, and 1,4-diazabicyclo[2.2.2]octane.
- Examples of other aliphatic amines include tris(2-methoxymethoxyethyl)amine, tris ⁇ 2-(2-methoxyethoxy)ethyl ⁇ amine, tris ⁇ 2-(2-methoxyethoxymethoxy)ethyl ⁇ amine, tris ⁇ 2-(1-methoxyethoxy)ethyl ⁇ amine, tris ⁇ 2-(1-ethoxyethoxy)ethyl ⁇ amine, tris ⁇ 2-(1-ethoxypropoxy)ethyl ⁇ amine, tris[2- ⁇ 2-(2-hydroxyethoxy)ethoxy ⁇ ethyl]amine and triethanolamine triacetate, and triethanolamine triacetate is preferable.
- an aromatic amine may be used as the component (D2).
- aromatic amines examples include 4-dimethylaminopyridine, pyrrole, indole, pyrazole, imidazole and derivatives thereof, as well as tribenzylamine, 2,6-diisopropylaniline and N-tert-butoxycarbonylpyrrolidine.
- component (D2) one type of compound may be used alone, or two or more types may be used in combination.
- the amount of the component (D2) is typically used in an amount within a range from 0.01 to 5 parts by weight, relative to 100 parts by weight of the component (A).
- the amount of the component (D) is within the above-mentioned range, the shape of the resist pattern and the post exposure stability of the latent image formed by the pattern-wise exposure of the resist layer are improved.
- At least one compound (E) (hereafter referred to as the component (E)) selected from the group consisting of an organic carboxylic acid, or a phosphorus oxo acid or derivative thereof may be added.
- Suitable organic carboxylic acids include acetic acid, malonic acid, citric acid, malic acid, succinic acid, benzoic acid, and salicylic acid.
- Examples of phosphorus oxo acids include phosphoric acid, phosphonic acid and phosphinic acid. Among these, phosphonic acid is particularly desirable.
- oxo acid derivatives include esters in which a hydrogen atom within the above-mentioned oxo acids is substituted with a hydrocarbon group.
- hydrocarbon group include an alkyl group of 1 to 5 carbon atoms and an aryl group of 6 to 15 carbon atoms.
- phosphoric acid derivatives examples include phosphoric acid esters such as di-n-butyl phosphate and diphenyl phosphate.
- phosphonic acid derivatives include phosphonic acid esters such as dimethyl phosphonate, di-n-butyl phosphonate, phenylphosphonic acid, diphenyl phosphonate and dibenzyl phosphonate.
- one type may be used alone, or two or more types may be used in combination.
- the amount of the component (E) is typically used in an amount within a range from 0.01 to 5 parts by weight, relative to 100 parts by weight of the component (A).
- the resist composition may further include a fluorine additive (hereafter, referred to as “component (F)”) for imparting water repellency to the resist film.
- component (F) a fluorine additive
- component (F) for example, a fluorine-containing polymeric compound described in Japanese Unexamined Patent Application, First Publication No. 2010-002870, Japanese Unexamined Patent Application, First Publication No. 2010-032994, Japanese Unexamined Patent Application, First Publication No. 2010-277043, Japanese Unexamined Patent Application, First Publication No. 2011-13569, and Japanese Unexamined Patent Application, First Publication No. 2011-128226 can be used.
- a structural unit derived from 1-ethyl-1-cyclooctyl (meth)acrylate or a structural unit derived from 1-methyl-1-adamantyl (meth)acrylate is preferable.
- examples of the halogen atom for Rf 102 and Rf 103 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is particularly desirable.
- examples of the alkyl group of 1 to 5 carbon atoms for Rf 102 and Rf 103 include the same alkyl group of 1 to 5 carbon atoms as those described above for R, and a methyl group or an ethyl group is preferable.
- halogenated alkyl group of 1 to 5 carbon atoms represented by Rf 102 or Rf 103 include groups in which part or all of the hydrogen atoms of the aforementioned alkyl groups of 1 to 5 carbon atoms have been substituted with halogen atoms.
- nf 1 represents an integer of 1 to 5, preferably an integer of 1 to 3, and more preferably 1 or 2.
- Rf 101 represents an organic group containing a fluorine atom, and is preferably a hydrocarbon group containing a fluorine atom.
- the hydrocarbon group containing a fluorine atom may be linear, branched or cyclic, and preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, and most preferably 1 to 10 carbon atoms.
- Rf 101 a fluorinated hydrocarbon group of 1 to 6 carbon atoms is preferable, and a trifluoromethyl group, —CH 2 —CF 3 , —CH 2 —CF 2 —CF 3 , —CH(CF 3 ) 2 , —CH 2 —CH 2 —CF 3 , and —CH 2 —CH 2 —CF 2 —CF 2 —CF 3 are most preferable.
- the weight average molecular weight (Mw) (the polystyrene equivalent value determined by gel permeation chromatography) of the component (F) is preferably 1,000 to 50,000, more preferably 5,000 to 40,000, and most preferably 10,000 to 30,000.
- Mw of the component (F) is no more than the upper limit of the above-mentioned range, the resist composition exhibits a satisfactory solubility in a resist solvent.
- the Mw is at least as large as the lower limit of the above-mentioned range, dry etching resistance and the cross-sectional shape of the resist pattern becomes satisfactory.
- the dispersity (Mw/Mn) of the component (F) is preferably 1.0 to 5.0, more preferably 1.0 to 3.0, and most preferably 1.2 to 2.5.
- component (F) one type may be used alone, or two or more types may be used in combination.
- the component (F) is used in an amount within a range from 0.5 to 10 parts by weight, relative to 100 parts by weight of the component (A).
- the resist composition of the present embodiment may be prepared by dissolving the resist materials for the resist composition in an organic solvent (hereafter, referred to as “component (S)”).
- the component (S) may be any organic solvent which can dissolve the respective components to give a homogeneous solution, and any organic solvent can be appropriately selected from those which have been conventionally known as solvents for a chemically amplified resist composition.
- component (S) examples include lactones such as ⁇ -butyrolactone; ketones such as acetone, methyl ethyl ketone, cyclohexanone, methyl-n-pentyl ketone, methyl isopentyl ketone, and 2-heptanone; polyhydric alcohols, such as ethylene glycol, diethylene glycol, propylene glycol and dipropylene glycol; compounds having an ester bond, such as ethylene glycol monoacetate, diethylene glycol monoacetate, propylene glycol monoacetate, and dipropylene glycol monoacetate; polyhydric alcohol derivatives including compounds having an ether bond, such as a monoalkylether (e.g., monomethylether, monoethylether, monopropylether or monobutylether) or monophenylether of any of these polyhydric alcohols or compounds having an ester bond (among these, propylene glycol monomethyl ether acetate (PGMEA) and propylene
- the component (S) can be used individually, or in combination as a mixed solvent.
- PGMEA PGMEA
- PGME ⁇ -butyrolactone
- EL cyclohexanone
- a mixed solvent obtained by mixing PGMEA with a polar solvent is preferable.
- the mixing ratio (weight ratio) of the mixed solvent can be appropriately determined, taking into consideration the compatibility of the PGMEA with the polar solvent, but is preferably in the range of 1:9 to 9:1, more preferably from 2:8 to 8:2.
- the PGMEA:EL or cyclohexanone weight ratio is preferably from 1:9 to 9:1, and more preferably from 2:8 to 8:2.
- the PGMEA:PGME weight ratio is preferably from 1:9 to 9:1, more preferably from 2:8 to 8:2, and still more preferably 3:7 to 7:3.
- a mixed solvent of PGMEA, PGME and cyclohexanone is also preferable.
- a mixed solvent of at least one of PGMEA and EL with ⁇ -butyrolactone is also preferable.
- the mixing ratio (former:latter) of such a mixed solvent is preferably from 70:30 to 95:5.
- the amount of the component (S) is not particularly limited, and is appropriately adjusted to a concentration which enables coating of a coating solution to a substrate.
- the component (S) is used in an amount such that the solid content of the resist composition becomes within the range from 1 to 20% by weight, and preferably from 2 to 15% by weight.
- a polymeric compound (A1) having a structural unit (a0) represented by general formula (a0-1) is used as the base component (A).
- the structural unit (a0) has an acid dissociable group represented by general formula (a0-r1-1) on the terminal of the side-chain thereof.
- the acid dissociable group contains a quaternary carbon atom (Ya 0 ) and a polar group.
- acid dissociable group containing a quaternary carbon atom (Ya 0 )
- acid dissociability upon exposure in the formation of a resist pattern may be reliably improved, as compared to the case where the acid dissociable group contains a tertiary carbon atom. Therefore, the reactivity may be improved, and sensitivity may be enhanced. In addition, a high dissolution contrast may be obtained by developing.
- solubility in a developing solution containing an organic solvent may be maintained at a low level. Therefore, in a solvent developing process, in the case where the acid dissociable group is not decomposed and remains at exposed portions of the resist film, or in the case where a decomposition product remains in the resist film, the dissolution rate of the exposed portions of the resist film in an organic developing solution may be suppressed from being increased, such that film loss of pattern portions may be suppressed. In addition, partial dissolution of pattern boundary portions may also be suppressed. Furthermore, by virtue of the acid dissociable group containing a polar group, the affinity for an alkali developing solution may be improved. Therefore, in an alkali developing process, by virtue of the solubility in an alkali developing solution being improved, developing may be proceeded more uniformly and more smoothly.
- CDU critical dimension uniformity
- circularity may be improved, and a resist pattern having a good shape may be formed.
- the method of forming a resist pattern according to the present embodiment includes: forming a resist film on a substrate using a resist composition of the first aspect; conducting exposure of the resist film; and developing the resist film to form a resist pattern.
- the method for forming a resist pattern according to the present embodiment may be performed, for example, as follows.
- a resist composition of the present embodiment is applied to a substrate using a spinner or the like, and a bake treatment (post applied bake (PAB)) is conducted at a temperature of 80 to 150° C. for 40 to 120 seconds, preferably 60 to 90 seconds, to form a resist film.
- a bake treatment post applied bake (PAB)
- PAB post applied bake
- baking treatment post exposure baking (PEB) is conducted under temperature conditions of 80 to 150° C. for 40 to 120 seconds, and preferably 60 to 90 seconds.
- the developing treatment is conducted using an alkali developing solution in the case of an alkali developing process, and a developing solution containing an organic solvent (organic developing solution) in the case of a solvent developing process.
- the rinse treatment is preferably conducted using pure water in the case of an alkali developing process, and a rinse solution containing an organic solvent in the case of a solvent developing process.
- the developing solution or the rinse liquid remaining on the pattern can be removed by a treatment using a supercritical fluid.
- bake treatment post bake
- the substrate is not specifically limited and a conventionally known substrate can be used.
- substrates for electronic components and such substrates having wiring patterns formed thereon can be used.
- Specific examples of the material of the substrate include metals such as silicon wafer, copper, chromium, iron and aluminum; and glass.
- Suitable materials for the wiring pattern include copper, aluminum, nickel, and gold.
- any one of the above-mentioned substrates provided with an inorganic and/or organic film on the surface thereof may be used.
- an inorganic antireflection film inorganic BARC
- an organic antireflection film organic BARC
- an organic film such as a lower-layer organic film used in a multilayer resist method can be used.
- a “multilayer resist method” is method in which at least one layer of an organic film (lower-layer organic film) and at least one layer of a resist film (upper resist film) are provided on a substrate, and a resist pattern formed on the upper resist film is used as a mask to conduct patterning of the lower-layer organic film.
- This method is considered as being capable of forming a pattern with a high aspect ratio. More specifically, in the multilayer resist method, a desired thickness can be ensured by the lower-layer organic film, and as a result, the thickness of the resist film can be reduced, and an extremely fine pattern with a high aspect ratio can be formed.
- the multilayer resist method is broadly classified into a method in which a double-layer structure consisting of an upper-layer resist film and a lower-layer organic film is formed (double-layer resist method), and a method in which a multilayer structure having at least three layers consisting of an upper-layer resist film, a lower-layer organic film and at least one intermediate layer (thin metal film or the like) provided between the upper-layer resist film and the lower-layer organic film (triple-layer resist method).
- the wavelength to be used for exposure is not particularly limited and the exposure can be conducted using radiation such as ArF excimer laser, KrF excimer laser, F 2 excimer laser, extreme ultraviolet rays (EUV), vacuum ultraviolet rays (VUV), electron beam (EB), X-rays, and soft X-rays.
- the resist composition of the present invention is effective to KrF excimer laser, ArF excimer laser, EB and EUV, and particularly effective to ArF excimer laser, EB and EUV.
- the exposure of the resist film can be either a general exposure (dry exposure) conducted in air or an inert gas such as nitrogen, or immersion exposure (immersion lithography).
- the immersion medium preferably exhibits a refractive index larger than the refractive index of air but smaller than the refractive index of the resist film to be exposed.
- the refractive index of the immersion medium is not particularly limited as long as it satisfies the above-mentioned requirements.
- Examples of this immersion medium which exhibits a refractive index that is larger than the refractive index of air but smaller than the refractive index of the resist film include water, fluorine-based inert liquids, silicon-based solvents and hydrocarbon-based solvents.
- the fluorine-based inert liquids include liquids containing a fluorine-based compound such as C 3 HCl 2 F 5 , C 4 F 9 OCH 3 , C 4 F 9 OC 2 H 5 or C 5 H 3 F 7 as the main component, which have a boiling point within a range from 70 to 180° C. and preferably from 80 to 160° C.
- a fluorine-based inert liquid having a boiling point within the above-mentioned range is advantageous in that the removal of the immersion medium after the exposure can be conducted by a simple method.
- a perfluoroalkyl compound in which all of the hydrogen atoms of the alkyl group are substituted with fluorine atoms is particularly desirable.
- these perfluoroalkyl compounds include perfluoroalkylether compounds and perfluoroalkylamine compounds.
- a suitable perfluoroalkylether compound is perfluoro(2-butyl-tetrahydrofuran) (boiling point 102° C.), and an example of a suitable perfluoroalkylamine compound is perfluorotributylamine (boiling point 174° C.).
- water is preferable in terms of cost, safety, environment and versatility.
- TMAH tetramethylammonium hydroxide
- any of the conventional organic solvents can be used which are capable of dissolving the component (A) (prior to exposure).
- the organic solvent include polar solvents such as ketone solvents, ester solvents, alcohol solvents, nitrile solvents, amide solvents and ether solvents, and hydrocarbon solvents.
- a ketone solvent is an organic solvent containing C—C( ⁇ O)—C within the structure thereof.
- An ester solvent is an organic solvent containing C—C( ⁇ O)—O—C within the structure thereof.
- An alcohol solvent is an organic solvent containing an alcoholic hydroxy group in the structure thereof.
- An “alcoholic hydroxy group” refers to a hydroxy group bonded to a carbon atom of an aliphatic hydrocarbon group.
- a nitrile solvent is an organic solvent containing a nitrile group in the structure thereof.
- An amide solvent is an organic solvent containing an amide group within the structure thereof.
- An ether solvent is an organic solvent containing C—O—C within the structure thereof.
- organic solvents have a plurality of the functional groups which characterizes the aforementioned solvents within the structure thereof.
- the organic solvent can be classified as any type of the solvent having the characteristic functional group.
- diethyleneglycol monomethylether can be classified as either an alcohol solvent or an ether solvent.
- a hydrocarbon solvent consists of a hydrocarbon which may be halogenated, and does not have any substituent other than a halogen atom.
- the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferable.
- organic solvent contained in the organic developing solution among these, a polar solvent is preferable, and ketone solvents, ester solvents and nitrile solvents are preferable.
- ketone solvents include 1-octanone, 2-octanone, 1-nonanone, 2-nonanone, acetone, 4-heptanone, 1-hexanone, 2-hexanone, diisobutyl ketone, cyclohexanone, methylcyclohexanone, phenylacetone, methyl ethyl ketone, methyl isobutyl ketone, acetylacetone, acetonylacetone, ionone, diacetonylalcohol, acetylcarbinol, acetophenone, methyl naphthyl ketone, isophorone, propylenecarbonate, ⁇ -butyrolactone and methyl amyl ketone (2-heptanone).
- a ketone solvent methyl amyl ketone (2-heptanone) is preferable.
- ester solvents include methyl acetate, butyl acetate, ethyl acetate, isopropyl acetate, amyl acetate, isoamyl acetate, ethyl methoxyacetate, ethyl ethoxyacetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monopropyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monophenyl ether acetate, diethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, 2-methoxybutyl acetate, 3-methoxybutyl acetate, 4-me
- nitrile solvents examples include acetonitrile, propionitrile, valeronitrile, butyronitrile and the like.
- the organic developing solution may have a conventional additive blended.
- the additive include surfactants.
- the surfactant is not particularly limited, and for example, an ionic or non-ionic fluorine and/or silicon surfactant can be used.
- a non-ionic surfactant is preferable, and a non-ionic fluorine surfactant or a non-ionic silicon surfactant is more preferable.
- the amount thereof based on the total amount of the organic developing solution is generally 0.001 to 5% by weight, preferably 0.005 to 2% by weight, and more preferably 0.01 to 0.5% by weight.
- the developing treatment can be performed by a conventional developing method.
- a conventional developing method examples thereof include a method in which the substrate is immersed in the developing solution for a predetermined time (a dip method), a method in which the developing solution is cast up on the surface of the substrate by surface tension and maintained for a predetermined period (a puddle method), a method in which the developing solution is sprayed onto the surface of the substrate (spray method), and a method in which the developing solution is continuously ejected from a developing solution ejecting nozzle while scanning at a constant rate to apply the developing solution to the substrate while rotating the substrate at a constant rate (dynamic dispense method).
- a dip method a method in which the developing solution is cast up on the surface of the substrate by surface tension and maintained for a predetermined period
- spray method a method in which the developing solution is sprayed onto the surface of the substrate
- dynamic dispense method a method in which the developing solution is continuously ejected from a developing solution ejecting
- any of the aforementioned organic solvents contained in the organic developing solution can be used which hardly dissolves the resist pattern.
- at least one solvent selected from the group consisting of hydrocarbon solvents, ketone solvents, ester solvents, alcohol solvents, amide solvents and ether solvents is used.
- at least one solvent selected from the group consisting of hydrocarbon solvents, ketone solvents, ester solvents, alcohol solvents and amide solvents is preferable, more preferably at least one solvent selected from the group consisting of alcohol solvents and ester solvents, and an alcohol solvent is particularly desirable.
- the alcohol solvent used for the rinse liquid is preferably a monohydric alcohol of 6 to 8 carbon atoms, and the monohydric alcohol may be linear, branched or cyclic. Specific examples thereof include 1-hexanol, 1-heptanol, 1-octanol, 2-hexanol, 2-heptanol, 2-octanol, 3-hexanol, 3-heptanol, 3-octanol, 4-octanol and benzyl alcohol. Among these, 1-hexanol, 2-heptanol and 2-hexanol are preferable, and 1 hexanol and 2-hexanol are more preferable.
- the organic solvent one kind of solvent may be used alone, or two or more kinds of solvents may be used in combination. Further, an organic solvent other than the aforementioned examples or water may be mixed together. However, in consideration of the development characteristics, the amount of water within the rinse liquid, based on the total amount of the rinse liquid is preferably 30% by weight or less, more preferably 10% by weight or less, still more preferably 5% by weight or less, and most preferably 3% by weight or less.
- the rinse solution may have a conventional additive blended.
- the additive include surfactants.
- the additive include surfactants.
- the surfactant the same surfactants as those described above can be mentioned, a non-ionic surfactant is preferable, and a non-ionic fluorine surfactant or a non-ionic silicon surfactant is more preferable.
- the amount thereof based on the total amount of the rinse liquid is generally 0.001 to 5% by weight, preferably 0.005 to 2% by weight, and more preferably 0.01 to 0.5% by weight.
- the rinse treatment using a rinse liquid can be conducted by a conventional rinse method.
- the rinse method include a method in which the rinse liquid is continuously applied to the substrate while rotating it at a constant rate (rotational coating method), a method in which the substrate is immersed in the rinse liquid for a predetermined time (dip method), and a method in which the rinse liquid is sprayed onto the surface of the substrate (spray method).
- the polymeric compound of the present invention includes a structural unit (a0) represented by general formula (a0-1) shown below.
- R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
- Va 0 represents a divalent hydrocarbon group which may have an ether bond;
- n a0 represents an integer of 0 to 2;
- Ra 00 represents an acid dissociable group represented by general formula (a0-r1-1);
- Ra 01 represents a hydrocarbon group which may have a substituent;
- Ra 02 represents a hydrocarbon group which may have a substituent; Ra 01 and Ra 02 may be mutually bonded to form a ring;
- Ya 0 represents a quaternary carbon atom;
- Ra 031 , Ra 032 and Ra 033 each independently represents a hydrocarbon group which may have a substituent; provided that at least one of Ra 031 , Ra 032 and Ra 033 is a hydrocarbon group having a polar group.
- a chain transfer agent such as HS—CH 2 —CH 2 —CH 2 —C(CF 3 ) 2 —OH may be used to introduce a —C(CF 3 ) 2 —OH group at the terminal(s) of the polymer.
- a copolymer having introduced a hydroxyalkyl group in which some of the hydrogen atoms of the alkyl group are substituted with fluorine atoms is effective in reducing developing defects and LER (line edge roughness: unevenness of the side walls of a line pattern).
- a monomer for deriving a structural unit (a0) may be produced, for example, by a method referring to the synthesis described at paragraphs 0087 and 0090 of WO2013/042,694.
- the resist composition of the present embodiment generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid.
- the component (A) is the same as defined for the component (A) described above regarding the resist composition of the first aspect.
- the component (A) contains a resin component (A1′) (hereafter, referred to as “component (A1′)”) which exhibits changed solubility in a developing solution by the action of acid.
- component (A) at least the component (A1′) is used, and a polymeric compound and/or a low molecular weight compound may be used in combination with the component (A1′).
- the component (A1′) has a structural unit (a0) represented by the aforementioned general formula (a0-1) and a structural unit (a10) represented by general formula (a10-1). If desired, the component (A1′) may include, in addition to the structural units (a0) and (a10), other structural unit.
- component (A1′) examples include a copolymer having a structural unit (a0), a structural unit (a10) and any other structural unit if desired (hereafter, this copolymer is sometimes referred to as “component (A1′-1)”).
- component (A1′) examples include a mixed resin of a copolymer having a structural unit (a0) and any other structural unit if desired (hereafter, this copolymer is sometimes referred to as “component (A1′-21)”) and a copolymer having a structural unit (a10) and any other structural unit if desired (hereafter, this copolymer is sometimes referred to as “component (A1′-22)”).
- the structural unit (a0) is represented by general formula (a0-1) above.
- the structural unit (a0) is the same as defined for the structural unit (a0) described above regarding the resist composition of the first aspect.
- structural unit (a0) contained in the component (A1′) 1 kind of structural unit may be used, or 2 or more kinds of structural units may be used.
- the amount of the structural unit (a0) based on the combined total (100 mol %) of all structural units constituting the component (A1′) is preferably 30 to 80 mol %, more preferably 40 to 75 mol %, still more preferably 50 to 70 mol %, and most preferably 50 to 60 mol %.
- the amount of the structural unit (a0) is at least as large as the lower limit of the above preferable range, a resist pattern may be reliably obtained, and various lithography properties such as resolution and roughness are further improved.
- the amount is no more than the upper limit of the above preferable range, a good balance may be achieved with the other structural units.
- the structural unit (a10) is a structural unit represented by general formula (a10-1) shown below.
- R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms
- Ya x1 represents a single bond or a divalent linking group
- Wa x1 represents an aromatic hydrocarbon group having a valency of (n ax1 +1); and n ax1 represents an integer of 1 or more.
- R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms.
- alkyl group having 1 to 5 carbon atoms for R a linear or branched alkyl group of 1 to 5 carbon atoms is preferable, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group and a neopentyl group.
- the halogenated alkyl group of 1 to 5 carbon atoms represented by R is a group in which part or all of the hydrogen atoms of the aforementioned alkyl group of 1 to 5 carbon atoms have been substituted with halogen atoms.
- the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is particularly desirable.
- a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a fluorinated alkyl group of 1 to 5 carbon atoms is preferable, and in view of industrial availability, a hydrogen atom, a methyl group or a trifluoromethyl group is more preferable, a hydrogen atom or a methyl group is still more preferable, and a methyl group is most preferable.
- Ya x1 represents a single bond or a divalent linking group.
- the divalent linking group for Ya x1 is not particularly limited, and preferable examples thereof include a divalent hydrocarbon group which may have a substituent and a divalent linking group containing a hetero atom.
- the hydrocarbon group may be either an aliphatic hydrocarbon group or an aromatic hydrocarbon group.
- aliphatic hydrocarbon group refers to a hydrocarbon group that has no aromaticity.
- the aliphatic hydrocarbon group may be saturated or unsaturated. In general, the aliphatic hydrocarbon group is preferably saturated.
- Examples of the aliphatic hydrocarbon group include a linear or branched aliphatic hydrocarbon group, and an aliphatic hydrocarbon group containing a ring in the structure thereof can be given.
- the linear aliphatic hydrocarbon group preferably has 1 to 10 carbon atoms, more preferably 1 to 6, still more preferably 1 to 4, and most preferably 1 to 3.
- a linear alkylene group is preferable. Specific examples thereof include a methylene group [—CH 2 —], an ethylene group [—(CH 2 ) 2 —], a trimethylene group [—(CH 2 ) 3 —], a tetramethylene group [—(CH 2 ) 4 -] and a pentamethylene group [—(CH 2 ) 5 —].
- the branched aliphatic hydrocarbon group preferably has 2 to 10 carbon atoms, more preferably 3 to 6, still more preferably 3 or 4, and most preferably 3.
- branched alkylene groups are preferred, and specific examples include various alkylalkylene groups, including alkylmethylene groups such as —CH(CH 3 )—, —CH(CH 2 CH 3 )—, —C(CH 3 ) 2 —, —C(CH 3 )(CH 2 CH 3 )—, —C(CH 3 )(CH 2 CH 2 CH 3 )—, and —C(CH 2 CH 3 ) 2 —; alkylethylene groups such as —CH(CH 3 )CH 2 —, —CH(CH 3 )CH(CH 3 )—, —C(CH 3 ) 2 CH 2 —, —CH(CH 2 CH 3 )CH 2 —, and —C(CH 2 CH 3 ) 2 —CH 2 —; alkyltrimethylene groups such as —CH(CH 3 )CH 2 CH 2 —, and —CH 2 CH(CH 3 )CH 2 —; and
- the linear or branched aliphatic hydrocarbon group may or may not have a substituent.
- substituents include a fluorine atom, a fluorinated alkyl group of 1 to 5 carbon atoms, and a carbonyl group.
- a cyclic aliphatic hydrocarbon group containing a hetero atom in the ring structure thereof and may have a substituent a group in which two hydrogen atoms have been removed from an aliphatic hydrocarbon ring
- a group in which the cyclic aliphatic hydrocarbon group is bonded to the terminal of the aforementioned chain-like aliphatic hydrocarbon group, and a group in which the cyclic aliphatic group is interposed within the aforementioned linear or branched aliphatic hydrocarbon group can be given.
- the linear or branched aliphatic hydrocarbon group the same groups as those described above can be used.
- the cyclic aliphatic hydrocarbon group preferably has 3 to 20 carbon atoms, and more preferably 3 to 12 carbon atoms.
- the cyclic aliphatic hydrocarbon group may be either a polycyclic group or a monocyclic group.
- the monocyclic aliphatic hydrocarbon group a group in which 2 hydrogen atoms have been removed from a monocycloalkane is preferable.
- the monocycloalkane preferably has 3 to 6 carbon atoms, and specific examples thereof include cyclopentane and cyclohexane.
- the polycyclic group a group in which 2 hydrogen atoms have been removed from a polycycloalkane is preferable, and the polycyclic group preferably has 7 to 12 carbon atoms. Examples of the polycycloalkane include adamantane, norbornane, isobornane, tricyclodecane and tetracyclododecene.
- the cyclic aliphatic hydrocarbon group may or may not have a substituent.
- substituents include an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a hydroxyl group and a carbonyl group.
- the alkyl group as the substituent is preferably an alkyl group of 1 to 5 carbon atoms, and more preferably a methyl group, an ethyl group, a propyl group, an n-butyl group or a tert-butyl group.
- the alkoxy group as the substituent is preferably an alkoxy group having 1 to 5 carbon atoms, more preferably a methoxy group, ethoxy group, n-propoxy group, iso-propoxy group, n-butoxy group or tert-butoxy group, and still more preferably a methoxy group or an ethoxy group.
- halogen atom for the substituent examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferable.
- halogenated alkyl group for the substituent examples include groups in which part or all of the hydrogen atoms within the aforementioned alkyl groups has been substituted with the aforementioned halogen atoms.
- the cyclic aliphatic hydrocarbon group may have part of the carbon atoms constituting the ring structure thereof substituted with a substituent containing a hetero atom.
- a substituent containing a hetero atom —O—, —C( ⁇ O)—O—, —S—, —S( ⁇ O) 2 — or —S( ⁇ O) 2 —O— is preferable.
- the aromatic hydrocarbon group is a hydrocarbon group having at least one aromatic ring.
- the aromatic ring is not particularly limited, as long as it is a cyclic conjugated compound having (4n+2) ⁇ electrons, and may be either monocyclic or polycyclic.
- the aromatic ring preferably has 5 to 30 carbon atoms, more preferably 5 to 20 carbon atoms, and still more preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms.
- the number of carbon atoms within a substituent(s) is not included in the number of carbon atoms of the aromatic hydrocarbon group.
- aromatic ring examples include aromatic hydrocarbon rings, such as benzene, naphthalene, anthracene and phenanthrene; and aromatic hetero rings in which part of the carbon atoms constituting the aforementioned aromatic hydrocarbon rings has been substituted with a hetero atom.
- hetero atom within the aromatic hetero rings include an oxygen atom, a sulfur atom and a nitrogen atom.
- aromatic hetero ring include a pyridine ring and a thiophene ring.
- aromatic hydrocarbon group examples include a group in which two hydrogen atoms have been removed from the aforementioned aromatic hydrocarbon ring or aromatic hetero ring (arylene group or heteroarylene group); a group in which two hydrogen atoms have been removed from an aromatic compound having two or more aromatic rings (biphenyl, fluorene or the like); and a group in which one hydrogen atom of the aforementioned aromatic hydrocarbon ring or aromatic hetero ring has been substituted with an alkylene group (a group in which one hydrogen atom has been removed from the aryl group within the aforementioned arylalkyl group such as a benzyl group, a phenethyl group, a 1-naphthylmethyl group, a 2-naphthylmethyl group, a 1-naphthylethyl group, or a 2-naphthylethyl group, or a heteroarylalkyl group).
- the hydrogen atom within the aromatic hydrocarbon group may be substituted with a substituent.
- the hydrogen atom bonded to the aromatic ring within the aromatic hydrocarbon group may be substituted with a substituent.
- substituents include an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, and a hydroxyl group.
- the alkyl group as the substituent is preferably an alkyl group of 1 to 5 carbon atoms, and more preferably a methyl group, an ethyl group, a propyl group, an n-butyl group or a tert-butyl group.
- the same groups as the aforementioned substituent groups for substituting a hydrogen atom within the cyclic aliphatic hydrocarbon group can be used.
- Ya x1 represents a divalent linking group containing a hetero atom
- the linking group include —O—, —C( ⁇ O)—O—, —O—C( ⁇ O)—, —C( ⁇ O)—, —O—C( ⁇ O)—O—, —C( ⁇ O)—NH—, —NH—, —NH—C( ⁇ NH)— (may be substituted with a substituent such as an alkyl group, an acyl group or the like), —S—, —S( ⁇ O) 2 —, —S( ⁇ O) 2 —O—, and a group represented by general formula: —Y 21 —O—Y 22 —, —Y 21 —O—, —Y 21 —C( ⁇ O)—O—, —C( ⁇ O)—Y 21 —, —[Y 21 —C( ⁇ O)—O] m′′ —Y 22 , —Y 21 —O—C(
- H may be substituted with a substituent such as an alkyl group, an acyl group or the like.
- the substituent an alkyl group, an acyl group or the like
- a linear aliphatic hydrocarbon group is preferable, more preferably a linear alkylene group, still more preferably a linear alkylene group of 1 to 5 carbon atoms, and a methylene group or an ethylene group is particularly desirable.
- m′′ represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and most preferably 1.
- the group represented by the formula —[Y 21 —C(O)—O] m ′′-Y 22 — is a group represented by the formula —Y 21 —C(O)—O—Y 22 —.
- a group represented by the formula —(CH 2 ) a′ —C( ⁇ O)—O—(CH 2 ) b′ — is preferable.
- a′ is an integer of 1 to 10, preferably an integer of 1 to 8, more preferably an integer of 1 to 5, still more preferably 1 or 2, and most preferably 1.
- b′ is an integer of 1 to 10, preferably an integer of 1 to 8, more preferably an integer of 1 to 5, still more preferably 1 or 2, and most preferably 1.
- a single bond, an ester bond [—C( ⁇ O)—O—, —O—C( ⁇ O)—], an ether bond (—O—), a linear or branched alkylene group, or a combination of these is preferable, and a single bond or an ester bond [—C( ⁇ O)—O—, —O—C( ⁇ O)—] is more preferable.
- Wa x1 represents an aromatic hydrocarbon group having a valency of (n ax1 +1).
- Examples of the aromatic hydrocarbon group for Wa x1 include a group obtained by removing (n ax1 +1) hydrogen atoms from an aromatic ring.
- the aromatic ring is not particularly limited, as long as it is a cyclic conjugated compound having (4n+2) ⁇ electrons, and may be either monocyclic or polycyclic.
- the aromatic ring preferably has 5 to 30 carbon atoms, more preferably 5 to 20 carbon atoms, and still more preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms.
- the aromatic ring examples include an aromatic hydrocarbon ring, such as benzene, naphthalene, anthracene or phenanthrene; and an aromatic heterocyclic ring in which part of the carbon atoms constituting the aromatic hydrocarbon ring has been substituted with a heteroatom.
- the hetero atom within the aromatic hetero rings include an oxygen atom, a sulfur atom and a nitrogen atom.
- Specific examples of the aromatic hetero ring include a pyridine ring and a thiophene ring.
- aromatic hydrocarbon group for Wa x1 examples include a group in which (n ax1 +1) hydrogen atom(s) has been removed from an aromatic group containing 2 or more aromatic rings (e.g., biphenyl, fluorene, or the like).
- Wa x1 a group in which (n ax1 +1) hydrogen atoms have been removed from benzene, naphthalene, anthracene or biphenyl is preferable, a group in which (n ax1 +1) hydrogen atoms have been removed from benzene or naphthalene is more preferable, and a group in which (n ax1 +1) hydrogen atoms have been removed from benzene is still more preferable.
- R ⁇ represents a hydrogen atom, a methyl group or a trifluoromethyl group.
- the amount of the structural unit (a10) is at least as large as the lower limit of the above preferable range, the sensitivity may be more reliably enhanced.
- the amount of the structural unit (a10) is no more than the upper limit of the above-mentioned range, a good balance may be reliably achieved with the other structural units.
- the component (A1′) may include, in addition to the structural units (a0) and (a10), other structural unit.
- Examples of the component (A1′) include a resin component containing the component (A1′-1), and a mixed resin containing the component (A1′-21) and the component (A1′-22).
- the component (A1′-1) is a copolymer having a structural unit (a0), a structural unit (a10) and any other structural unit if desired.
- the amount of the structural unit (a0) based on the combined total (100 mol %) of all structural units constituting the component (A1′-1) is preferably 30 to 80 mol %, more preferably 40 to 75 mol %, still more preferably 50 to 70 mol %, and most preferably 50 to 60 mol %.
- the amount of the structural unit (a10) based on the combined total (100 mol %) of all structural units constituting the component (A1′-1) is preferably 20 to 70 mol %, more preferably 25 to 60 mol %, still more preferably 30 to 50 mol %, and most preferably 40 to 50 mol %.
- the other structural unit examples include the structural unit (a1), structural unit (a2) and structural unit (a3).
- the amount of the other structural unit(s) based on the combined total (100 mol %) of all structural units constituting the component (A1′-1) is preferably more than 0 mol % to 25 mol %.
- the weight average molecular weight (Mw) (the polystyrene equivalent value determined by gel permeation chromatography (GPC)) of the component (A1′-1) is not particularly limited, but is preferably 1,000 to 50,000, more preferably 2,000 to 30,000, and still more preferably 3000 to 20,000.
- the resist composition exhibits a satisfactory solubility in a resist solvent.
- the Mw is at least as large as the lower limit of the above-mentioned preferable range, dry etching resistance and the cross-sectional shape of the resist pattern becomes satisfactory.
- the molecular weight dispersity (Mw/Mn) of the component (A1′-1) is not particularly limited, but is preferably 1.0 to 4.0, more preferably 1.0 to 3.0, and most preferably 1.0 to 2.5.
- Mn is the number average molecular weight.
- the mixed resin contains the component (A1′-21) and the component (A1′-22).
- the component (A1′-21) is a polymer having a structural unit (a0) and other structural unit, if desired.
- the amount of the structural unit (a0) based on the combined total (100 mol %) of all structural units constituting the component (A1′-21) is preferably 30 mol % or more, more preferably 40 to 75 mol %, and still more preferably 50 to 70 mol %.
- the other structural unit examples include the structural unit (a1), structural unit (a2) and structural unit (a3).
- the amount of the other structural unit(s) based on the combined total (100 mol %) of all structural units constituting the component (A1′-21) is preferably more than 0 mol % to 50 mol %.
- the weight average molecular weight (Mw) (the polystyrene equivalent value determined by gel permeation chromatography (GPC)) of the component (A1′-21) is not particularly limited, but is preferably 1,000 to 50,000, more preferably 2,000 to 30,000, and still more preferably 3000 to 20,000.
- the component (A1′-22) is a polymer having a structural unit (a10) and other structural unit, if desired.
- the amount of the structural unit (a10) based on the combined total (100 mol %) of all structural units constituting the component (A1′-22) is preferably 20 mol % or more, more preferably 25 to 60 mol %, and still more preferably 30 to 50 mol %.
- the other structural unit examples include the structural unit (a1), structural unit (a2) and structural unit (a3).
- the amount of the other structural unit(s) based on the combined total (100 mol %) of all structural units constituting the component (A1′-22) is preferably more than 0 mol % to 80 mol %.
- the weight average molecular weight (Mw) (the polystyrene equivalent value determined by gel permeation chromatography (GPC)) of the component (A1′-22) is not particularly limited, but is preferably 1,000 to 50,000, more preferably 2,000 to 30,000, and still more preferably 3000 to 20,000.
- the ratio of the component (A1′-21) to the component (A1′-22) in terms of weight ratio (A1′-21)/(A1′-22) is preferably 5/95 to 95/5, more preferably 10/90 to 90/10, and still more preferably 15/85 to 85/15.
- the amount of the component (A1′) based on the total weight of the component (A) is preferably 50% by weight or more, more preferably 75% by weight or more, still more preferably 90% by weight or more, and may be even 100% by weight.
- the amount of the component (A1′) is at least as large as the lower limit of the above preferable range, sensitivity may be improved, and a resist pattern with improved lithography properties such as resolution and reduced roughness may be reliably formed.
- component (A2) a base component which exhibits changed solubility in a developing solution under action of acid
- component (A2) a base component which exhibits changed solubility in a developing solution under action of acid
- component (A2) there is no particular limitation, and any of the multitude of conventional base resins used within chemically amplified resist compositions may be arbitrarily selected for use.
- component (A2) one kind of a polymer or a low molecular weight compound may be used, or a combination of two or more kinds may be used.
- the amount of the component (A) may be appropriately adjusted depending on the thickness of the resist film to be formed, and the like.
- the resist composition of the present embodiment may contain, in addition to the aforementioned component (A), any other components other than the component (A).
- the other components include the component (B), the component (D), the component (E), the component (F) and the component (S) described above in relation to the resist composition of the first aspect.
- the resist composition of the present embodiment employs a resin component (A1′) including two kinds of structural units having specific structures, namely, a structural unit (a0) represented by general formula (a0-1) and a structural unit (a10) represented by general formula (a10-1).
- the structural unit (a10) functions as a proton source.
- the acid dissociable group represented by general formula (a0-r1-1) contained in the structural unit (a0) exhibits a high reaction efficiency to acid, and is reliably dissociated, as compared to a conventional acid dissociable group. Therefore, by using a resist composition containing the component (A1′), both sensitivity and resolution may be improved.
- the acid dissociable group represented by general formula (a0-r1-1) has a bulky structure and is highly hydrophilic. Therefore, by using a resist composition containing the component (A1′), a good development contrast may be reliably obtained, and the roughness of the pattern may be reduced.
- the resist composition of the present embodiment sensitivity can be enhanced in the formation of a resist pattern, and it becomes possible to form a resist pattern exhibiting excellent lithography properties (resolution, reduction of roughness, and the like).
- the resist composition of the present embodiment particularly in the method of forming a resist pattern using extreme ultraviolet (EUV) or electron beam (EB) as an exposure source, both high sensitivity and good lithography properties (resolution, reduced roughness, etc.) may be satisfied.
- EUV extreme ultraviolet
- EB electron beam
- the method for forming a resist pattern according to the present embodiment may be performed, for example, in the same manner as in the method described above for the method of forming a resist pattern according to the second aspect.
- the wavelength of the light used for exposure is not particularly limited.
- the resist composition of the fourth aspect may be particularly useful for EB or EUV lithography.
- sensitivity may be improved.
- lithography properties resolution, reduction of roughness, and the like
- the copolymer of the present embodiment has a structural unit represented by general formula (a0-1) shown below and a structural unit represented by general formula (a10-1) shown below.
- R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
- Va 0 represents a divalent hydrocarbon group which may have an ether bond;
- n a0 represents an integer of 0 to 2;
- Ra 00 represents an acid dissociable group represented by general formula (a0-r1-1);
- Ra 01 represents a hydrocarbon group which may have a substituent;
- Ra 02 represents a hydrocarbon group which may have a substituent; Ra 01 and Ra 02 may be mutually bonded to form a ring;
- Ya 0 represents a quaternary carbon atom;
- Ra 031 , Ra 032 and Ra 033 each independently represents a hydrocarbon group which may have a substituent; provided that at least one of Ra 031 , Ra 032 and Ra 033 is a hydrocarbon group having a polar group;
- * represents a valence bond.
- R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms
- Ya x1 represents a single bond or a divalent linking group
- Wa x1 represents an aromatic hydrocarbon group having a valency of (n ax1 +1); and n ax1 represents an integer of 1 or more.
- the amount of the structural unit (a0) based on the combined total (100 mol %) of all structural units constituting the copolymer is preferably 30 to 80 mol %, more preferably 40 to 75 mol %, still more preferably 50 to 70 mol %, and still more preferably 50 to 60 mol %.
- the amount of the structural unit (a10) based on the combined total (100 mol %) of all structural units constituting the copolymer is 20 to 70 mol %, preferably 25 to 60 mol %, more preferably 30 to 50 mol %, and still more preferably 40 to 50 mol %.
- the copolymer according to the present embodiment is the same as defined for the component (A1′-1) (copolymer including a structural unit (a0), a structural unit (a10), and any other structural unit, if desired) described above, and the kind of each structural unit other than the structural units (a0) and (a10), the amount of each structural unit and the like are the same as defined above for the component (A1′-1).
- the copolymer of the present embodiment may be produced, for example, dissolving a monomer which derives a structural unit (a0), a monomer which derives a structural unit (a10) and, if desired, a monomer which derives a structural unit other than the structural units (a0) and (a10) in a polymerization solvent, followed by adding a radical polymerization initiator such as azobisisobutyronitrile (AIBN) or dimethyl 2,2′-azobis(isobutyrate) (V-601) to effect a polymerization reaction.
- a radical polymerization initiator such as azobisisobutyronitrile (AIBN) or dimethyl 2,2′-azobis(isobutyrate) (V-601)
- the copolymer of the present embodiment may be produced by dissolving a monomer which derives a structural unit (a0), a monomer which ultimately derives a structural unit (a10) by a deprotection reaction of the protected alcohol portion following the polymerization, and, if desired, a monomer which derives a structural unit other than the structural units (a0) and (a10) in a polymerization solvent, followed by adding a radical polymerization initiator such as azobisisobutyronitrile (AIBN) or dimethyl 2,2′-azobis(isobutyrate) (V-601) to effect a polymerization reaction, and conducting a suitable deprotection reaction of the obtained polymer to form the structural unit (a10).
- a radical polymerization initiator such as azobisisobutyronitrile (AIBN) or dimethyl 2,2′-azobis(isobutyrate) (V-601)
- a chain transfer agent such as HS—CH 2 —CH 2 —CH 2 —C(CF 3 ) 2 —OH may be used to introduce a —C(CF 3 ) 2 —OH group at the terminal(s) of the polymer.
- a copolymer having introduced a hydroxyalkyl group in which some of the hydrogen atoms of the alkyl group are substituted with fluorine atoms is effective in reducing developing defects and LER (line edge roughness: unevenness of the side walls of a line pattern).
- a monomer for deriving a structural unit (a0) may be produced, for example, by a method referring to the synthesis described at paragraphs 0087 and 0090 of WO2013/042694.
- the copolymer according to the present embodiment is a novel substance useful as a base resin for a resist composition.
- the copolymer may be preferably added to a resist composition as a base component having a film forming ability, and also as a resin component (component (A1′)) which exhibits changed solubility in a developing solution by the action of acid.
- the obtained monomer (a01) was analyzed by NMR, and the structure thereof was identified by the following results.
- the resulting reaction liquid was heated while stirring for 1 hour, and then the reaction liquid was cooled to room temperature.
- the resulting polymer solution was dropwise added to an excess amount of n-heptane to precipitate a polymer. Then, the precipitated white powder was separated by filtration, followed by drying, thereby obtaining 6.7 g of an objective polymeric compound (A1-1).
- the weight average molecular weight (Mw) and the polydispersity (Mw/Mn) were determined by the polystyrene equivalent value as measured by gel permeation chromatography (GPC). As a result, it was found that the weight average molecular weight was 7,900, and the polydispersity was 1.61.
- (A2)-1 Polymeric compound represented by chemical formula (A2-1) shown below.
- the weight average molecular weight (Mw) and the dispersity (Mw/Mn) in terms of the polystyrene equivalent value measured by gel permeation chromatography (GPC) were 7,000 and 1.50, respectively.
- (A2)-2 Polymeric compound represented by chemical formula (A2-2) shown below.
- the weight average molecular weight (Mw) and the dispersity (Mw/Mn) in terms of the polystyrene equivalent value measured by gel permeation chromatography (GPC) were 7,500 and 1.48, respectively.
- (B)-1 A compound (acid generator) represented by chemical formula (B-1) shown below.
- (D)-1 A compound (diffusion control agent) represented by chemical formula (D-1) shown below.
- (F)-1 fluorine-containing polymeric compound represented by chemical formula (F-1) below.
- the weight average molecular weight (Mw) and the dispersity (Mw/Mn) in terms of the polystyrene equivalent value measured by gel permeation chromatography (GPC) were 15,500 and 1.67, respectively.
- PEB post exposure bake
- the resist composition of Example 1 could improve sensitivity and lithography properties, and a resist pattern having a good shape could be formed.
- the obtained monomer (a02) was analyzed by NMR, and the structure thereof was identified by the following results.
- the weight average molecular weight (Mw) and the polydispersity (Mw/Mn) were determined by the polystyrene equivalent value as measured by gel permeation chromatography (GPC). As a result, it was found that the weight average molecular weight was 7,000, and the polydispersity was 1.6.
- Copolymers (A1′-1-2) to (A1′-1-5) were produced in the same manner as in “Production example of copolymer (A1′-1-1)”, except that monomers for deriving the structural units that constitute each copolymer were used in a predetermined molar ratio.
- Copolymers (A2′-1) to (A2′-5) were produced in the same manner as in “Production example of copolymer (A1′-1-1)”, except that monomers for deriving the structural units that constitute each copolymer were used in a predetermined molar ratio.
- the weight average molecular weight (Mw) and the polydispersity (Mw/Mn) were determined by the polystyrene equivalent value as measured by gel permeation chromatography (GPC). As a result, it was found that the weight average molecular weight was 7,000, and the polydispersity was 1.6.
- compositional ratio of the polymers (the molar ratio of the respective structural units in the polymeric compound) as determined by 13 C-NMR, the weight average molecular weight (Mw) and the polydispersity (Mw/Mn) determined by the polystyrene equivalent value as measured by GPC are also shown in Table 3.
- (a101) indicates p-hydroxystyrene.
- EESt p-ethoxyethoystyrene
- Each of the resist compositions of examples and comparative examples was applied to an 8-inch silicon substrate which had been treated with hexamethyldisilazane (HMDS) using a spinner, and was then prebaked (PAB) on a hot plate at 110° C. for 60 seconds and dried, thereby forming a resist film having a film thickness of 50 nm.
- HMDS hexamethyldisilazane
- the resist film was subjected to drawing (exposure) using an electron beam lithography apparatus JEOL JBX-9300FS (manufactured by JEOL Ltd.) at an acceleration voltage of 100 kV, targeting a 1:1 line and space pattern (hereafter, referred to as “L/S pattern”) having lines with a width of 50.
- a post exposure bake (PEB) treatment was conducted at 110° C. for 60 seconds.
- TMAH tetramethylammonium hydroxide
- the critical resolution (nm) with the above Eop was determined using a scanning electron microscope (product name: S-9380, manufactured by Hitachi High-Technologies Corporation). Specifically, the exposure dose was gradually increased from the optimum exposure dose Eop, and the minimum size of the pattern which resolves without collapse (fall) was determined. The results are indicated under “Resolution (nm)” in Table 5.
- 3 ⁇ indicates a value of 3 times the standard deviation ( ⁇ ) (i.e., 3 ⁇ ) (unit: nm) determined by measuring the line positions at 400 points in the lengthwise direction of the line using a scanning electron microscope (product name: S-9380, manufactured by Hitachi High-Technologies Corporation; acceleration voltage: 800V).
- the resist compositions of Examples 2 to 6 could improve sensitivity and enable formation of a resist pattern exhibiting good lithography properties (resolution and reduced roughness).
- Apparatus high vacuum RIE apparatus (product name: TCA-2400; manufactured by Tokyo Ohka Kogyo Co., Ltd.).
- Gas a mixed gas of oxygen gas (60 vol %) and nitrogen gas (40 vol %).
- sccm refers to a value as measured under 1 atm (atmospheric pressure: 1,013 hPa) at 23° C.)
- Etching rate was 600 nm/min or less
Abstract
Description
In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Va0 represents a divalent hydrocarbon group which may have an ether bond; na0 represents an integer of 0 to 2; Ra00 represents an acid dissociable group represented by general formula (a0-r1-1); Ra01 represents a hydrocarbon group which may have a substituent; Ra02 represents a hydrocarbon group which may have a substituent; Ra01 and Ra02 may be mutually bonded to form a ring; Ya0 represents a quaternary carbon atom; Ra031, Ra032 and Ra033 each independently represents a hydrocarbon group which may have a substituent; provided that at least one of Ra031, Ra032 and Ra033 is a hydrocarbon group having a polar group; * represents a valence bond.
In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Va0 represents a divalent hydrocarbon group which may have an ether bond; na0 represents an integer of 0 to 2; Ra00 represents an acid dissociable group represented by general formula (a0-r1-1); Ra01 represents a hydrocarbon group which may have a substituent; Ra02 represents a hydrocarbon group which may have a substituent; Ra01 and Ra02 may be mutually bonded to form a ring; Ya0 represents a quaternary carbon atom; Ra031, Ra032 and Ra033 each independently represents a hydrocarbon group which may have a substituent; provided that at least one of Ra031, Ra32 and Ra033 is a hydrocarbon group having a polar group; * represents a valence bond.
In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Va0 represents a divalent hydrocarbon group which may have an ether bond; na0 represents an integer of 0 to 2; Ra00 represents an acid dissociable group represented by general formula (a0-r1-1); Ra01 represents a hydrocarbon group which may have a substituent; Ra02 represents a hydrocarbon group which may have a substituent; Ra01 and Ra02 may be mutually bonded to form a ring; Ya0 represents a quaternary carbon atom; Ra031, Ra032 and Ra033 each independently represents a hydrocarbon group which may have a substituent; provided that at least one of Ra031, Ra032 and Ra033 is a hydrocarbon group having a polar group; * represents a valence bond.
In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Yax1 represents a single bond or a divalent linking group; Wax1 represents an aromatic hydrocarbon group having a valency of (nax1+1); and nax1 represents an integer of 1 or more.
In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Va0 represents a divalent hydrocarbon group which may have an ether bond; na0 represents an integer of 0 to 2; and Ra00 represents an acid dissociable group represented by general formula (a0-r1-1).
In the formula, Ra01 represents a hydrocarbon group which may have a substituent; Ra02 represents a hydrocarbon group which may have a substituent; Ra01 and Ra02 may be mutually bonded to form a ring; Ya0 represents a quaternary carbon atom; Ra031, Ra032 and Ra033 each independently represents a hydrocarbon group which may have a substituent; provided that at least one of Ra031, Ra032 and Ra033 is a hydrocarbon group having a polar group; and “*” represents a valence bond (in the present specification, the same applies hereafter).
[Chemical Formula 8]
*Ra04—Ra05)n
In the formula, Ra04 represents a divalent hydrocarbon group having 2 to 12 carbon atoms; Ra05 represents a divalent linking group containing a hetero atom; Ra06 represents a monovalent hydrocarbon group having 1 to 12 carbon atoms; and np0 represents an integer of 1 to 6.
In the formula, Yaa represents a carbon atom; Xaa represents a group which forms a cyclic hydrocarbon group together with Yaa; Ya0 represents a quaternary carbon atom; Ra0311 and Ra0321 each independently represents a chain alkyl group which may have a substituent; and Ra0331 is a functional group represented by the aforementioned general formula (a0-p 1).
In the formula, Ra′4 to Ra′6 each independently represents a hydrocarbon group, provided that Ra′5 and Ra′6 may be mutually bonded to form a ring.
In the formulae, Ra′10 represents an alkyl group of 1 to 10 carbon atoms; Ra′11 is a group which forms an aliphatic cyclic group together with a carbon atom having Ra′10 bonded thereto; and Ra′12 to Ra′14 each independently represents a hydrocarbon group.
In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Va1 represents a divalent hydrocarbon group which may contain an ether bond; na1 represents an integer of 0 to 2; and Ra1 represents an acid dissociable group represented by the aforementioned formula (a1-r-1) or (a1-r-2). Wa1 represents a hydrocarbon group having a valency of na2+1; na2 represents an integer of 1 to 3; and Raz represents an acid dissociable group represented by the aforementioned formula (a1-r-1) or (a1-r-3).
In the formulae, each Ra′51 independently represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, —COOR″, —OC(═O)R″, a hydroxyalkyl group or a cyano group; R″ represents a hydrogen atom, an alkyl group, a lactone-containing cyclic group, a carbonate-containing cyclic group or an —SO2— containing cyclic group; A″ represents an oxygen atom, a sulfur atom, or an alkylene group of 1 to 5 carbon atoms with or without an oxygen atom or a sulfur atom;
In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Ya21 represents a single bond or a divalent linking group; La21 represents —O—, —COO—, —CON(R′)—, —OCO—, —CONHCO— or —CONHCS—; and R′ represents a hydrogen atom or a methyl group; provided that, when La21 represents —O—, Ya21 does not represent —CO—; and Ra21 represents a lactone-containing cyclic group, an —SO2— containing cyclic group or a carbonate-containing cyclic group.
In the formulas, R is the same as defined above; j is an integer of 1 to 3; k is an integer of 1 to 3; t′ is an integer of 1 to 3; 1 is an integer of 1 to 5; and s is an integer of 1 to 3.
In the formulae, V′101 represents a single bond or an alkylene group of 1 to 5 carbon atoms; V′102 represents a divalent saturated hydrocarbon group of 1 to 30 carbon atoms.
In the formulae, each R′201 independently represents a hydrogen atom, a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent.
In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Va0 represents a divalent hydrocarbon group which may have an ether bond; na0 represents an integer of 0 to 2; Ra00 represents an acid dissociable group represented by general formula (a0-r1-1); Ra01 represents a hydrocarbon group which may have a substituent; Ra02 represents a hydrocarbon group which may have a substituent; Ra01 and Ra02 may be mutually bonded to form a ring; Ya0 represents a quaternary carbon atom; Ra031, Ra032 and Ra033 each independently represents a hydrocarbon group which may have a substituent; provided that at least one of Ra031, Ra032 and Ra033 is a hydrocarbon group having a polar group.
In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Va0 represents a divalent hydrocarbon group which may have an ether bond; na0 represents an integer of 0 to 2; Ra00 represents an acid dissociable group represented by general formula (a0-r1-1); Ra01 represents a hydrocarbon group which may have a substituent; Ra02 represents a hydrocarbon group which may have a substituent; Ra01 and Ra02 may be mutually bonded to form a ring; Ya0 represents a quaternary carbon atom; Ra031, Ra032 and Ra033 each independently represents a hydrocarbon group which may have a substituent; provided that at least one of Ra031, Ra032 and Ra033 is a hydrocarbon group having a polar group; * represents a valence bond.
In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Yax1 represents a single bond or a divalent linking group; Wax1 represents an aromatic hydrocarbon group having a valency of (nax1+1); and nax1 represents an integer of 1 or more.
TABLE 1 | |||
Component (A) |
Component | Component | Component | Component | Component | Component | ||
(A1) | (A2) | (B) | (D) | (F) | (S) | ||
Example 1 | (A1)-1 | — | (B)-1 | (D)-1 | (F)-1 | (S)-1 |
[100] | [6.0] | [4.0] | [3.0] | [3650] | ||
Comparative | — | (A2)-1 | (B)-1 | (D)-1 | (F)-1 | (S)-1 |
Example 1 | [100] | [6.0] | [4.0] | [3.0] | [3650] | |
Comparative | — | (A2)-2 | (B)-1 | (D)-1 | (F)-1 | (S)-1 |
Example 2 | [100] | [6.0] | [4.0] | [3.0] | [3650] | |
Comparative | — | (A2)-3 | (B)-1 | (D)-1 | (F)-1 | (S)-1 |
Example 3 | [100] | [6.0] | [4.0] | [3.0] | [3650] | |
Comparative | — | (A2)-4 | (B)-1 | (D)-1 | (F)-1 | (S)-1 |
Example 4 | [100] | [6.0] | [4.0] | [3.0] | [3650] | |
TABLE 2 | |||||
PAB | PEB | Eop | CDU | Circularity | |
(° C.) | (° C.) | (mJ/cm2) | (nm) | (nm) | |
Example 1 | 110 | 80 | 14.4 | 4.4 | 2.7 |
Comparative | 110 | 80 | 20.9 | 5.2 | 3.1 |
Example 1 | |||||
Comparative | 110 | 80 | 17.3 | 4.9 | 2.9 |
Example 2 | |||||
Comparative | 110 | 80 | 21.2 | 5.5 | 2.7 |
Example 3 | |||||
Comparative | 110 | 80 | 16.5 | 5.7 | 2.4 |
Example 4 | |||||
TABLE 3 | |||
Ratio of structural unit derived | Weight average | Poly- | |
from each monomer | molecular weight | dispersity | |
Copolymer | (molar ratio) | (Mw) | (Mw/Mn) |
(A1′-1-1) | (a101)/(a01) = 50/50 | 7000 | 1.6 |
(A1′-1-2) | (a101)/(a01) = 45/55 | 7000 | 1.6 |
(A1′-1-3) | (a101)/(a01) = 40/60 | 7000 | 1.6 |
(A1′-1-4) | (a101)/(a02) = 40/60 | 7000 | 1.6 |
(A1′-1-5) | (a21)/(a101)/(a01) = | 7000 | 1.6 |
20/30/50 | |||
(A2′-1) | (a101)/(a11) = 50/50 | 7000 | 1.6 |
(A2′-2) | (a101)/(a12) = 50/50 | 7000 | 1.6 |
(A2′-3) | (a101)/(a13) = 50/50 | 7000 | 1.6 |
(A2′-4) | (a101)/(a14) = 50/50 | 7000 | 1.6 |
(A2′-5) | (a101)/(a15) = 50/50 | 7000 | 1.6 |
(A2′-6) | (a21)/(a01) = 50/50 | 7000 | 1.6 |
TABLE 4 | ||||
Component | Component | Component | Component | |
(A) | (B) | (D) | (S) | |
Example 2 | (A′)-1 | (B)-1 | (D)-1 | (S)-1 |
[100] | [14] | [3] | [5700] | |
Example 3 | (A′)-2 | (B)-1 | (D)-1 | (S)-1 |
[100] | [14] | [3] | [5700] | |
Example 4 | (A′)-3 | (B)-1 | (D)-1 | (S)-1 |
[100] | [14] | [3] | [5700] | |
Example 5 | (A′)-4 | (B)-1 | (D)-1 | (S)-1 |
[100] | [14] | [3] | [5700] | |
Example 6 | (A′)-5 | (B)-1 | (D)-1 | (S)-1 |
[100] | [14] | [3] | [5700] | |
Comparative | (A′)-6 | (B)-1 | (D)-1 | (S)-1 |
Example 5 | [100] | [14] | [3] | [5700] |
Comparative | (A′)-7 | (B)-1 | (D)-1 | (S)-1 |
Example 6 | [100] | [14] | [3] | [5700] |
Comparative | (A′)-8 | (B)-1 | (D)-1 | (S)-1 |
Example 7 | [100] | [14] | [3] | [5700] |
Comparative | (A′)-9 | (B)-1 | (D)-1 | (S)-1 |
Example 8 | [100] | [14] | [3] | [5700] |
Comparative | (A′)-10 | (B)-1 | (D)-1 | (S)-1 |
Example 9 | [100] | [14] | [3] | [5700] |
Comparative | (A′)-11 | (B)-1 | (D)-1 | (S)-1 |
Example 10 | [100] | [14] | [3] | [5700] |
TABLE 5 | |||||
PAB | PEB | Eop | Resolution | LWR | |
(° C.) | (° C.) | (mJ/cm2) | (nm) | (nm) | |
Example 2 | 110 | 110 | 65 | 25 | 6.5 |
Example 3 | 110 | 110 | 66 | 25 | 6.3 |
Example 4 | 110 | 110 | 69 | 24 | 6.2 |
Example 5 | 110 | 110 | 71 | 25 | 6.3 |
Example 6 | 110 | 110 | 70 | 25 | 6.1 |
Comparative | 110 | 110 | 86 | 35 | 7.7 |
Example 5 | |||||
Comparative | 110 | 110 | 70 | 32 | 8.1 |
Example 6 | |||||
Comparative | 110 | 110 | 55 | 30 | 8.9 |
Example 7 | |||||
Comparative | 110 | 110 | 90 | 35 | 6.9 |
Example 8 | |||||
Comparative | 110 | 110 | 72 | 30 | 7.5 |
Example 9 | |||||
Comparative | 110 | 110 | 88 | 30 | 6.3 |
Example 10 | |||||
TABLE 6 | |||
Etching resistance | |||
Example 2 | A | ||
Example 3 | A | ||
Example 4 | A | ||
Example 5 | B | ||
Example 6 | A | ||
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TW201829492A (en) | 2018-08-16 |
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US20190219920A1 (en) | 2019-07-18 |
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